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The Day Sara Was Born

by saralove

The Day Sara Was Born

The Day Sara was Born[i]

By saralove

It was a dark chilly stormy April day. I was in my sophomore year in college. I walked towards the library that Friday afternoon depressed that yet again, I had no date for the weekend. I was skinny, insecure, and pale white. There was a torrent of sexual activity going on all around me. I could literally feel and sense its presence, but I was excluded from participation. So, I went to the very top floor of the library. I’d never been there before, but it was the most remote, and I just wanted to be alone.

After an hour or so in the books I got up to go to the men’s room. I was constipated and would be there a while. There were two stalls. One was occupied, so I took the other. As I settled into the stall, I was surprised by all the sexual graffiti on the wall but paid it little mind. I then notice a quarter sized hole had been carved out of the walls between the two stalls.

A few minutes later, I was surprised to notice that the occupant from the other stall hadn’t left. I felt the slightest urge to look through the hole to see what he was doing but couldn’t summon the courage. So instead, I leaned forward the get a better angle back towards him. It was then that I noticed a rapid jerking movement through the opening. Where my next sensation came from to this day I have no idea, but a beautiful paralyzing rush, in equal parts excitement and terror, gripped my stomach as I realized that the guy in the stall next to me was masturbating. I tried to control the raggedness of my breath, but for a few seconds my breathing had to be audible to him. I sat there confused, not knowing what I was going to do next. Without really thinking about it I started to play with myself. In no time I was rock hard.

It was at this point that the excitement overtook the terror, and I knew I had to take a closer look. For what seemed like an eternity I moved my eye closer to the hole. I was in an awkward position leaning over like that, but I managed to keep my balance as I traversed the last few inches between the hole and my eye. What I saw next would change my whole life.

I had a perfect angle down onto his lap. His pants were down by his knees. He had slowed his pace into a soft caress. His shaft was straight, thick, pink and long. I could see the glisten of a drop of pre-cum at the tip of his thick bulbous head. On a soft downstroke the full length of his cock was exposed.

I lost track of time. Then I realized I’d been staring at this guy’s cock for…how long I don’t know. I got scared. I wanted to look away. But I couldn’t. I realized that I was staring at this marvelous thing not at all for the idle curiosity which had inspired my first distant view through the hole. I was staring at it because I wanted it…desperately.

Having been met by nothing but frustration in trying to find a girl, the thought occurred to me how hot it would be to be a girl… his girl. It was then that the disjointed feelings I was experiencing coalesced into the first sweet sissy perversion I’d ever felt. This was such a jarring sensation I finally leaned back and stroked my relatively small cock. I know he could hear my breathing now, and there was no use in trying to control the sound of it.

I gradually composed myself. He was still there. Was he there for me? Did the idea of having sex with me turn him on? The possibility that anyone might be turned on by the idea of having sex with me was a powerful intoxicant. Still there was nothing but silence from the stall next to me.

So, I was presented with a conundrum.

What to do?

Soon enough I knew I had to see that cock one more time. This time I would look at it with purpose and calculation. I would commit its image in every detail to memory….the size of the head, the veins in the shaft… I knew there was no way I had the courage to make the first move, so to speak, but at the very least I could go back to my room and in the gathering darkness I could masturbate to a powerful orgasm while thinking of this splendid cock.

So again, I approached the hole. This time, with more resolve. Had I again approached slower I might have seen what was waiting for me there, but I didn’t. When I pinned my eye against the hole, I found myself staring right into the unblinking eye of my companion in the stall next to me.

I recoiled in horror. I’d had my first gay/sissy urge not five minutes ago and already I’d been “found out”. I hurriedly pulled up my pants and ran out of the bathroom back to my seat. My face must’ve been beet red, and if anybody had bothered to notice me, they could’ve instantly seen what a wreck I was.

I stared at the door to the men’s room, which was in plain view of my table. Finally, the door opened, and I returned my stare intently down at my books, doing my best to appear absorbed in my studies and not the least bit interested in who was emerging from the men’s room. It was then that I realized to my horror there was no one else in the general vicinity but he and I.

He walked towards and then past my table on his way to the elevator. I never dared look up. As he passed, though, he strummed his fingers on my table.

He knew it was me. And he knew that I knew that he knew.  Mortified, I kept my head buried in the book until I heard him get on the elevator and depart. I then noticed I was covered with sweat.

I let a few minutes pass. Then I gathered my things and left. I went back to my apartment. I could hear a couple having sex through the thin walls of my apartment. As always before, I focused on the sounds the girl was making…but as never before, I focused on those sounds not to create the fantasy of doing her wondering what she was feeling; wondering what it would be like to possess her charms. And I would notice in the days to come that I would do such things without premeditation or purpose .My default first reaction to any heterosexual stimuli whether in real life or on television or in magazines was to imagine being the girl.

I thought again of the beautiful cock I had stared at that afternoon. I knew what I wanted to do. I wanted to dress like a girl and suck on a dildo……maybe even try to ease it inside me. Here, alone in my apartment, where I could safely act as girly as I wanted, and no one would notice.

There was a huge sex shop on the edge of town. I drove out there and rode around for several minutes to satisfy myself that no one I knew was there. I then dashed from the car to the door, looking around all the time, terrified that I’d be noticed. I went in. I guess it was the mirrored windows, but inside suddenly I felt safe…secure. I had planned to rush around and get the things I’d come for, but I looked around the store. No one else was rushing about. No one else even cared that I was there. Everyone looked relaxed. So, I did the same.

I carefully considered a number of different sets of lingerie, finally settling on three sets that I liked the best. I also got a waitress and cheerleader outfit.

Then I went to the back room of the store where an entire wall was devoted to dildos of every shape, size, and color imaginable. I set about searching for the one that reminded me most of the penis I’d seen that afternoon, and though it took a while I found the perfect match. I stared down at it longingly and felt a bulge in my pants. I wanted it in my pants, rubbing against my ass cheeks. All of a sudden, I couldn’t wait to get back home. So, I headed to check out. Along the way I passed a counter of exotic lubricants. Thinking of the full range of uses to which I intended to put the dildo, I picked up a few bottles of that as well.

Then an awful thought occurred to me. I actually have to take these items up to the counter, panties, girly outfits, a dildo and some lube, and check them out. It was one thing to be found out by an unknown stranger who obviously shared at least some part of my perversion in a bathroom stall, but here I was…in a brightly lit store…with several other customers milling around…holding my panties and girly outfits and lube and dildo. Looking around I was relieved to see that no one seemed to notice, or care. But I froze in horror when I saw that the cash register was tended by a really hot chick…the kind that never looked at me except dismissively. She became a metaphor for every girl who had rejected me, for every girl who unknown to me, must have laughed at the ridiculous thought of me with no clothes on. I now had to go before her and by tendering these items for purchase declare to her and all the girls she represented in my mind that I was giving up on being a man…that I had joined the most laughable, contemptible, ridiculous, humiliating and lowest caste in the world of sex, a sissy faggot crossdressing boy.

My first reaction was to feel a re-emergence of my male impulses…put this stuff away; don’t give up the fight; be a man. But as I pondered that option, I grew weary at the remembrance of all the past failures…I soon realized that these strange, new, and intoxicating sensations had rushed upon the shore of my sexuality like a tidal wave and had washed away whatever weakening resolve I had to continue to wage that losing battle.

My second reaction was to realize that, for the second time that day, I was frozen between terror and ecstasy. I was so close to living out these newfound fantasies in the privacy of my apartment that I could taste it. But I couldn’t even work up the image of having the courage to actually approach the checkout counter and present these items…to her… for purchase. I don’t know how much time passed as I made a series of false starts to the counter, but finally I resolved to give up and go home empty handed. It was then that the calculus was no longer one of fear vs. ecstasy, but the fear of the embarrassment of actually purchasing these items vs. the fear of going through this long rainy night alone…yes, I actually thought of being with this dildo as being not alone.

Then I knew what I had to do, and that I was only prolonging the agony by my procrastination. So, I began again, my final assault on the checkout counter. I was actually going to cross the Rubicon into a strange new and unexplored world of desires and with luck, at long last, fulfillment of those desires.

I placed the items on the countertop, and fumbled for my wallet, looking down. The checkout girl, to my great surprise, cheerfully said hello, and complimented my selections…like she meant it. I looked up and thanked her. She said she’d actually purchased the lavender teddy and panties for herself, and it drove her boyfriend wild. After several more minutes of friendly back and forth as she rang up my purchase, it dawned upon me that she was talking to me like I played for her team, and not a pathetic specimen of the opposite sex that had to be discouraged through impatience, dismissive expressions, voice inflection, or just looking right through him as if he wasn’t even there. That became clear when she cooed a bit over the dildo, and with a wicked grin, asked if I’d like batteries to go with it. Nervously, I said sure. She then said, “You’re new to this. aren’t you?” I blushed. “Relax, she said “You’re cool with me. I’ve been watching you since you came in.” I felt a flood of relief wash over me….rather than cruel rejection,  had I found a kindred spirit or at least a kind soul?

She then said, “Let me recommend one more item.” She pulled out a tiny brown bottle. I asked her what it was. “Right when you’re ready to take his cock in your mouth, take a long hit of this...like you would with cocaine, or pot. You’ll love it.” Wow, I thought. So, she just assumed I was a cocksucker, and with a tone of her voice you’d expect her to use if she’d said, “Right when you’re ready to flip the steaks…”  Plus, my new playground comes with its own designer drugs.

She then asked, “Have you been with a guy before?”

“No”, I replied. I told her that I’d just planned to go home and dress up and experiment.

“So, you’ve never cross-dressed before?” she asked.

“No”, I replied.

“What kind of girl do you want to be?” she asked.

“What do you mean?”

“Blond, brunette, redhead…that sort of thing, ” she answered.

“Hadn’t thought about it. Blonde, I guess.”

“Wait right here”, she said.

A few minutes later she came back with a blonde wig, make-up and a skull cap. Nervously, I ventured, “I have no idea how to use this stuff.”

“You’ll learn,” she said.

“How?” I asked.

She stopped and looked at me for a minute. I noticed in her eyes a mixture of affection and concern. What she said next surprised me. “Would you like for me to show you?”

“You’d do that?” I replied

Look, she said, “I get off at 6:00. I’m meeting my boyfriend at 9:00. I’ve got three hours. That’s plenty of time.”

I stammered a bit but told her I’d love her help. “Where do you live?” she asked. Without even thinking that I might be falling into a cruel trap, I gave her my address and apartment number.

“Good”, she said. “I’ll be over by 6:15″

I rushed back to my apartment. I carefully laid all of my purchases on the bed. I put the wig and makeup on my desk and re-positioned a mirror from the bathroom over the desk to create a makeshift vanity. I looked at the clock. It was 5:45. To settle my nerves I took a beer from the refrigerator and reflected on the afternoon’s events. I had gone from being a frustrated heterosexual male college student to someone who was about to invite a total stranger into his apartment to dress him up like a girl.

I got up and went to the mirror. I tried to imagine myself as a girl, without much luck. I was just going to look silly by the time she got through with me, I thought. Then I wondered, “Why is she doing all this for me?” Why, after no girl had ever before done a nice thing for me in my whole miserable life, was this total stranger coming over to my apartment?”

For the third time that day, I was paralyzed with fear. Maybe it was a set up. Maybe she’d get me all dolled up, and then open the door for her boyfriend and his buddies, and they’d all have a good laugh at my expense. I sat in my desk chair, motionless. She knew where I lived. There was no sense in not answering the door when she came. If it was a cruel prank, they had me. I decided I had to ride this crazy train wherever it would lead. There was no going back at this point. Besides, I admitted to myself, I wanted it so much. I wanted to find out what would happen when she came into my apartment.

Then I heard the knock on the door.

I peered through the peephole and was relieved to see that she appeared to be by herself. I opened the door, “Heyyy”, she said, and gave me a quick hug.

“Come on in”, I said.

We walked back into my bedroom. She saw how I had set up my study desk as an impromptu vanity and smiled. Weakly, I asked, “OK. What do I do?”

She replied, “First off, we need to have an understanding. As between the two of us, you are a girl, not a boy. This process will require you to be naked around me, and I’m doing this with your promise that you will never try to make an advance on me as a boy. We’re strictly girlfriends…like suitemates.”

“Agreed” I replied.

“OK. The first thing we need to do is to assess the strengths and weaknesses in your feminine presentation. And to do that, I need to see you completely naked. With a rush of excitement, I complied.

“Turn around” she said. “Now put your hands on your hips and cock your ass, slightly……good. Ok, now I want you to walk away from me, and sway your hips like you’re a girl.”

I followed her instructions. She thought for a minute, and asked, “What’s your name?”

“Josh”, I replied.

“I’m Sally. Now what’s your sissy name? You get to choose that one yourself.”

Hadn’t really thought of that. After a short while, I settled on Sara.

“Sara’s great,” she said, “And from now on, I’ll call you Sara. OK?”

“Great”, I replied.

“Sara”, she said, “You have real potential. You have almost no body hair. You have thin hips, and creamy white skin. You’re face looks male, but it is without any pronounced male features like a big forehead or square jaw, so there is probably nothing there we can’t overcome with makeup. The thing we need to work on the most are movements and mannerisms. In other words, you walk like a guy.”

“I’m just afraid I’m going to look ridiculous by the time you’re finished with me”

“Well, there’s only one way to find out….Sara, why don’t you put on the cream negligee, hose and panties.”

As I put on these sweet nothings, I became aroused. The stockings felt so soft and cool. The tip of my cock peeked out of the top of my panties. I saw Sally notice, and she smiled.

After complying with a few preliminary instructions, she sat me down to apply the makeup. Starting with the foundation, she showed me every step along the way. As we progressed, I became engrossed with the transformation that was occurring in the mirror below me. When we were finished, I was literally stunned at how feminine my face looked.

She noticed my delight. ”Wait till I get that wig on you Sara. You’re going to be a real doll….close your eyes.”

I felt her position the skull cap, and then put on the wig.

I opened my eyes and stared in pure wonderment at the girl in the mirror. I was plain and nondescript as a guy. I was a walking streak of sex as a girl.

I let out a squeal of delight. Sally appeared quite pleased with herself.

Then she said, “We’re not yet finished. Stand up and pull down your panties.”

She pulled some tape out if her pocket. and to my great surprise, cupped my erect penis in her hand. It was rock hard.

“This is a problem”, she said. “I need it soft”

“The only thing I know to do is to masturbate. I’m so turned on right now I can come in no time.” I suggested.

She looked up at me. A wry smile crossed her lips. “I’ve got a better idea.”


“Sara, can you keep a secret?”


With that, she grabbed my hips with her hands and moved me to her face. She took my balls into her mouth and slowly worked her tongue up my tiny shaft. She boobed on the head of my cock and swallowed me in the sucking wetness of her mouth. Her tongue was everywhere. In no time I came, and she swallowed every bit of it. I looked down at her face. She didn’t seem the least bit turned on. Instead, she looked as if she’d just completed a pleasant enough but basically necessary task. And unintentionally she taught me for all time that my pee pee could never excite a woman….I accepted this understanding not with regret, but with a reaffirmation of a previously subconscious idea. For all time, I really needed to become a woman myself.

My cock then shriveled, and she expertly showed me how to wrap my cock and balls and tape them into my ass, I put the panties back on. There was no bulge at all. I looked just like an anatomical woman.

Then, her phone rang. It was her boyfriend. I heard her say, “Let me ask”.

She then said, “Sara, how far do you want to carry this tonight?”

“What do you mean?”

“That’s George on the phone. He knows what I’m doing. Sara…George is bisexual. So is his friend Sam. They are both tops…Do you know what a top is?”

“No” I stammered.

“Basically, it means when they’re with another guy they like to be the guy, and for the other guy to be the girl.”

“Sara, they want to come over and meet you……. Sara….they want to do you.”

I felt a new and strange arousal. Having just come, my dick was soft. It was void of any sensation, but I was so turned on. Even though I could not muster the nerve to mouth the word yes, my face must have been screaming yes.

Sally smiled and said, “Come on over, guys.”

Sally stripped down to her underwear and we softly began to kiss each other. I tickled her wet clit with my fingers. Then she said, “Let’s unlock the door and let them walk in on us like this.” I quickly agreed.

As we waited, we softly caressed each other. I wondered what lay ahead. I asked how I looked. ”Immaculate.” Sally replied.

It seemed like it took an eternity for them to get there, but we finally heard them walk in. Silently, Sam walked around to the end of the bed and said, “Come here, Sara. I want to show you something.”

I flipped over on my belly which brought me face to face with his crotch. Was I really about to do this?

“Why don’t you unzip my jeans?” he asked, and my heart froze.

As I reached up to comply, I was surprised at how dainty…how feminine… my hands looked. When his pants fell to the floor, within inches of my lipstick coated lips was a gorgeous, thick, slightly bent semi-erect cock. In ecstasy…no, a place beyond ecstasy, I softly ticked his balls and shaft with my fingers. In no time Sam had a raging erection.

The next thing I felt was Sally on my back, her breasts softly pressing down on me.

“Remember what I told you to do right before you take his cock into your mouth?” she asked.

I next saw the little brown bottle next to my nose, the top removed. I had no idea what to expect, but I inhaled long and deep from the bottle.

At first nothing…but then an exploding ball of excitement rising from the pit of my stomach and expanding through my brain. I looked ahead at Sam’s cock. I thought I’d wanted it before, but suddenly, sucking Sam’s cock was more than a matter of desire, it felt more important than breathing. My heart pounding, I wrapped my wet lips around his shaft and sucked long and deep. Sam moaned. It felt…indescribable? The shape… the texture… the taste….Like from birth my mouth had been put on this earth to hold such a thing within the wet suction of my lips, my tongue, all the way back to the entrance to my throat and beyond. My God. His cock was all the way in. My nostrils were pressed against his pubic hairs. I felt a strange warm sensation from head to toe. Whatever I had sniffed was powerful, and it turned desire into compulsion. His head was down in my throat. I wanted it to stay there forever. Why wasn’t I gagging? Later that evening, as we all rested in the afterglow, Sally would say it’s because I’m a natural…a natural cocksucker. When she said it, I would be filled with pride….perverse sissy pride. For the first time in my life, I had sexual currency.

Back in the moment, Sam pulled away. He didn’t want to come so fast. Drool flowed down out of my mouth across my chin. As he pulled out my mouth impulsively leaned forward in a vain attempt to recapture him. I looked over to see Sally sucking on George. I watched his cock as her lips flowed like silk up and down the shaft. I felt a strong bond of sisterhood with her. These two men were going to fuck us senseless, and we were going to share that together.

My breathing was ragged now as I reclined back on the bed to wait for what would come next. Sam slid in bed beside me, and we began to make out, my hands clutching his broad tanned back, his cock pressed against my panties. I spread my legs slightly. Taking the cue, Sam began to dry hunch me. I wrapped my legs around him. Then, unexpectedly, I felt George’s cock rub against my ass, and a moment later I was a sissy sandwich. My legs went limp. Cock was everywhere…down there. They loosened their grip a bit and I fell back, fondling both men.

Sally then said, “Sara, Sam and I are going to show you how to fuck.” I was jarred by her directness, and also that she would be doing this with Sam. We really were one big happy love family.

Sara got on her back and pulled off her panties. She had the cutest little cunt, and I felt a pang of jealousy. Sam hoisted her legs high into the air, exposing her asshole, as I lay on my side looking at them. George again pressed his raging erection against my ass.

To my great surprise, Sam took some of the lube I’d bought at the store and slowly went to work on Sally’s anus. Then I realized what Sally meant. She was going to show ME how to fuck…in the only way I could. And it was apparent from George’s enthusiastic thrusts against my backside that he intended to be the first beneficiary of my newly acquired skills.

Slowly Sam worked one finger, then two, into Sally’s ass. Her hips bucked. Sam pulled out the dildo and gently pressed the head against Sally’s lubed anus. He then propped Sally’s head up, and she took a long slow drag from the brown bottle. She laid back and her asshole instantly relaxed. Soon the dildo was thrusting in and out, rhythmically, methodically. Sally looked pleased as she played with her clit. Sam then removed the dildo, and propped Sally’s ass up on two pillows. Her asshole was now at the perfect angle to receive his cock. Sam mounted her, and Sally moaned. As his thrusts grew deeper and more purposeful, she let out a collage of squeals and moans and gasps that seemed like its own language…the language of anal sex. In the midst of this, and with no warning, Sam removed himself, and flipped Sally over on his tummy. I had become so engrossed in what I was watching that I only then noticed that George had pulled my panties down below my ass, and the head of his lubed cock was gently probing my hole. I wanted it…I think.

As Sam resumed working Sally over, she reached out and held my hand. She pulled me closer and kissed me tenderly as Sam plunged in and out of her ass. Her expression was a strange admixture of crazed ecstasy and sublime submission. After we kissed, she handed me the bottle. “Take two really long hits, and take care of my George for me, sweetheart. Can you do that for Sally?”

I felt great desire but also a sense of duty to do as my new best friend…my sister…had asked. I unscrewed the top and complied. Before I even finished the second drag that familiar rush I’d felt a few minutes ago started to come over me. And as before, I no longer just wanted George’s cock, I was compelled to bury it deep within my nether regions. He plunged inside me. He flipped me over on my belly. I was now laying beside Sally. I looked at her, and I soon discovered the same moans and squeals coming from my own throat as I’d heard coming from hers. Now we were both speaking the strange new language. We looked at each other, as our asses were both deliciously ravaged by cock. We bucked together, we moaned together, we stared deeply into each other’s eyes. I felt George’s thrusts take on new urgency. I returned my focus to him. With his cock buried deep inside my ass, I felt an explosion of warm thick semen into my belly…three huge shots, and then a fading fourth and fifth. I had nothing to compare it to, but what an incredible cumload.

Later, we talked for hours before we all fell into a blissful sleep on my king-size bed.

I was eternally a sissy cock worshipping whore…I had become this thing over the course of one day that had been nothing but miserable and humiliating until it unexpectedly became sweet, mysterious and deliciously perverted. falling to sleep, I positioned my mouth in front of Sam’s now flaccid cock, got comfortable, and gently suckled on him. I tasted Sally, I tasted his cum, I tasted the earthy combination of all things cock. And I drifted off. – to be continued.



[i] Originally published on February 26,2012 at annamalicesissyselfhypnosis.com as  #1000 – Sissy Story 29 – Sara by Sara -written by Annamalice contributor and devoted follower Sara, now warpmymind.com member saralove. An archived link to the original publication follows:




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