I felt the final shackle click into place around my left wrist. I was now completely restrained, helpless, and completely at her mercy…
As her note instructed, at 10:15 in the morning on Saturday the 3rd of May and a full week since she discovered me in her apartment, I crossed the hall to her door and knocked. I teetered there on the heels that were far too high and noticed that my very bare smooth legs were cold. I felt a breeze up the all too short skirt and knew that someone had left the door to the building open again.
But that was not my first worry. My first worry was that any one of the 28 doors in our hallway could open and out would walk someone I knew and who knew me, at least in passing. And they would see me, in the very filled out short pink dress and heels with the little frilly socks, 4 inch gold hoops peeking out from my hair. An outfit that anyone glancing down the hall would most certainly look twice at. And…I would be discovered by more people than just her.
I knocked again at what seemed to me to be two years waiting and saw the peep hole on her door go dark as she look out. After another maddening period I heard her start playing with the chain, then the bolt and finally the door opened and she stood there with an appraising eye on me.
I moved to push past her, but she stopped me with an upturned hand. The panic in my eyes had to be plain because she got a wicked smile on her beautiful face. The upturned hand became a single finger making a twirling motion at me. I was certainly starting to hyperventilate and felt quite light headed, but managed to understand that she wanted me to turn around for her to see me.
I managed a little feminine pirouette, which was what it was as turning around in a “manly” fashion in 4 inch heels is quite impossible. She giggled and pulled me to safety, shutting the door as I leaned against the wall my heart ready to burst through my tight dress and ample bust line. I don’t normally have a bust line. That came courtesy of a box delivered with the note. A box that contained very realistic weighty breast forms. I am not a stranger to these devices, but these were the best I had ever seen with small tape circles that went over my nipples and a glue that attached them quite firmly to my chest. Somewhere in them was a battery because when I touched the nipples, I felt an electric transfer to my own nipple underneath. And the firmness of the touch matched the intensity of the electric shock sent to my poor unsuspecting nipple underneath. Even the forms moving inside the bra I wore gave some sensation and that along with the weight of them pulling on my upper body created a very constant interesting sensation akin to what I imagine having breasts might actually be like. Honestly, it was amazing…until she turned to me and gave the left nipple a hard pinch. I jumped and yelped and she laughed.
“Oh my God, Andy, those are perfect! I love them!” she said with delight reaching for the other nipple as I shied away from her eager grabbing fingers. It didn’t work and the resulting shock raised another cry from me. Her entrance way was curtained off for some reason giving me very little room to maneuver in. She pushed me into the corner by the door and leaned her weight against me looking up into my face.
“Good, makeup on the eyes looks great, and you got your right ear pierced like I asked. Good! Those earrings look great on you.“ she said with a wink and I felt her hand go under my skirt and down my leg.
“Nice and smooth, just like a girl should be. Very nice. I like the dress with the boobs so much more, don’t you?” She said as her finger traced the lines of my panties…her panties until last week…under the dress that formerly belonged to her as well. “Yes…yes you will do nicely…” She purred.
She moved back and my arms moved up protectively of my breasts. Her eyes sparkled at the motion but she gestured to the curtains blocking off my view of her apartment.
“Do you like my new decorations?” she asked. I nodded slowly, not speaking as the note had instructed. Another smile played across her lips as she read my compliance with her wishes.
“I can’t have you seeing all I have prepared this past week until just the right time.” She said reaching into the back pocket of her jeans.
She produced a pink satin eye mask with an inch of white lace all the way around. It looked like a woman’s sleep mask and had open made up eyes painted on the front of the satin.
She held it out to me and said. “Put this on sweetie, and we will have so much fun together.”
-Seven Days Earlier-
I pressed the button on the remote and the fucking machine came to life…so fast that the dildo ramming into my ass hurt a LOT. I jerked forward in the restraints, my free wrist slamming into the bar. The shackle swung to the end of its hinges and bounced back, clicking into place…my wrist inside. I was trapped!
Her face registered shock and surprise at finding me in her living room, wearing her clothes, locked into her fucking machine…which was really beginning to get uncomfortable. Lube is only meant to last so long…
“Oh my God…Andy? What the hell?!” she exclaimed. Emotions played across her face; shock, surprise, anger…
I looked up at her, tears forming in my eyes “Sarah, I am so sorry! I didn’t mean…” My words trailed off. Clearly I did mean.
She was not supposed to be here, not coming back until Monday morning. Here it was Saturday afternoon and I thought I was safe. Safe to violate her privacy (you ass…), explore her things (bastard). My surprise at finding a fucking machine with harness in her closet was no less than her surprise at finding me now.
She walked over to her bedroom door and looked in, had to see some of her lingerie and more racy clothing laid out on the bed.
I kept blubbering that I was sorry…so sorry… I kept pulling at the left shackle, trying to work my hand free like I had been doing for the past 45 minutes…until her key turned in the lock.
Her shoe appeared by my left hand and I stopped dead still, tears falling. She squatted down and her hand raised my tear stained face. Traces of anger still played on her features.
“Sorry you did it, or sorry you got caught?” she asked.
“Yes” I whispered…to both. My heart hurt. It had all come to this. If only I could be…my fault for giving in to the need.
My answer seemed to take her aback, or maybe it was the misery on my face. She stood up and walked around a bit, not saying anything. When she came to the power cord for the machine, she pulled it out of the wall and it thankfully ceased its invasion, still inside of me.
I saw only her back as she opened the curtains and looked out the window for a minute. Finally, she turned and looked back at me and I ducked my head.
“Please, please just let me out…I’ll go away. I’ll go away and never bother you again. I promise!” I said quietly, my shame complete.
She replied “Those aren’t my shoes...”
She walked over and squatted down to examine the shoes – black patent strappy sandals with a 4-inch heel, and the little frilly socks, also mine.
“Those are cute.” She remarked and stood again moving out of my view into the bedroom.
I called out “Sarah, please….” But she seemed to take no notice.
She returned to the room several minutes later and said “The makeup must be yours too because you didn’t mess with mine.”
Sarah went to her roller bag, bent over and produced a camera. “Smile sweetie…” she said and began snapping pictures as I protested to no avail.
She grabbed one of her kitchen chairs and brought it to sit in front of me. I was angry now, chastened at my folly and desperate to feel anything but the helplessness I had always felt.
She sat, saw my outrage, and wagged her finger snapping, “No, you…you don’t get to be angry ANDY. YOU invaded my private area, took MY things, and got YOURSELF in this mess. YOU were just supposed to come in twice to water my PLANTS! Not drag all my shit out and indulge yourself in fulfilling your private fucking fantasy in my LIVING ROOM! I could SO have you arrested for this…”
The tears came again, but and I looked up at her and said quietly, “I shouldn’t have done this…I violated your privacy and I AM sorry Sarah. I will go away and leave you alone forever, I promise. Just please…please let me go and please don’t call the police! I didn’t mean any harm to you I swear! I just…” And again, my words faltered.
“Are you a cross dresser or a transsexual?” she asked and I looked up sharply.
“I…am transsexual” I said hesitantly, feeling shame I knew I shouldn’t. And then with a bit of wonder asked, “You know what that is?”
She nodded and looked at me considering. Finally she rose, and went behind me. The collar shackle prevented me from turning my head to see behind me. I felt the smooth dildo come out of my ass as she retracted the shaft of the machine, and she began undoing the shackles. My legs were unstable from being on hands and knees for over an hour and the heels made it impossible for me to move without assistance. When I was free, she helped me to rise and had me sit in the chair.
She went into the kitchen while I sat massaging my legs. She returned a short time later with a glass of water and another chair which she sat in, handing me the water. I accepted it and felt my eyes get hot with tears again at this act of human kindness from this woman I had so violated.
She smiled and said “Close your legs sweetie, you are giving me a total panty shot.” She smiled again and laughed as I shyly closed my legs and pulled at the fringe of the pink skirt, and somehow, I laughed a little too a heady rush of dizziness coming over me at all the rapid fire emotions of the past minutes. It all drained away and suddenly I was just wiped…mentally, emotionally, physically.
Sarah said “You know, I don’t know what to do about all this. I need some time to think.” She looked sharply at me and added “And so…do you.”
She leaned forward resting her elbows on her knees. “You are transgendered?” she asked again. I nodded and said quietly “All my life.” I looked away, but I felt her searching my face.
After a few more moments she said “Wow..so many questions.” She stood up. “Okay Andy, I am sending you home. Now look at me and LISTEN.” She said, her tone compelling me to look into her eyes.
“You…are not to go ANYWHERE. You will not leave, you will not try to flee, understand?” she asked.
I nodded slowly.
“You ARE going to go to the basement and wash my dress and panties and have them ready for me tonight…at nine I think.” She continued, “I am coming over to your place at nine and we will have a little chat. Do you understand?”
I nodded slowly in dawning disbelief.
“You need to think a lot about today and what it all means. And I want to see all your girl clothes, makeup, accessories…everything you have. Do you understand?” she asked.
I nodded slowly again sure I was in some sort of trap more secure than the harness had ever been.
She nodded too then and smiled “Good…good! We will talk and we will look at your things and we will….well, we will decide what to do next.”
I opened my mouth to ask what she meant about “deciding what to do next” but she shushed me and stared moving me to the door. I gestured to the corner…”Uh…my clothes, I should change…”
She shook her head “No…”
I said…”My uh…keys…my door is locked. In, in the pocket of my jeans…”
She kept pushing me to the door. “I will get them and toss them to you once you are at your door.”
“But…what if someone sees me?” I asked, my heart starting to race. “Someone already has.” She replied, and continued “You are going to cross the hall in that outfit to your place. You are going to wait there for me to toss you your keys…only then will you go inside. Do you understand?”
I nodded slowly, panic showing on my face as I teetered backwards to her door, her finger on my chest.
She opened her door and pushed me out. My head whipped around both directions to see if the hallway contained anyone. It did not.
Sarah gestured and said, “To your door…go…go…”
I went and stood exposed and looking back at her in panic. She smiled and finally turned around and disappeared inside. Seconds seemed like years as I huddled by my door hoping desperately that no one would come out and see me. Finally Sarah appeared and tossed me the key ring into the middle of the hallway forcing me to mince forward to retrieve the keys.
As I bent she commented “Oh, up skirt!” and laughed.
I darted back to my door and started fumbling with the keys.
Sarah said sharply and loudly, “Andy!” I turned aghast dropping the keys my eyes wide as saucers.
“See you at nine sweetie.” She said and winked at me, closing her door.
“Put this on sweetie, and we will have so much fun together.” she said.
I looked at the pink satin mask with some trepidation. All of this was so unguardedly feminine…and felt forbidden and well…dangerous. Not to life and limb, but certainly Sarah clearly intended to insert herself into my life and have a say and possibly her way. That…could upset a lot of things and it scared me terribly.
She saw my fear.
“Andy.” She said. “You remember our conversation last week?”
I nodded.
She continued “How this plays out is completely up to you. You can walk away at any time…but if you haven’t figured it out by now, I don’t ride passively through anything. Walking IS and will always be your choice…but if we are going to explore this together, how it plays out is going to be completely up….to me… Do you understand?”
I nodded again.
I searched her face as she said “I know you are scared. I get that. We are in ‘taboo land’ and you are the one exposed…but you are not alone.“
I took the beautiful mask from her hand and put it over my eyes.
I heard her sharp intake of breath and suddenly she was pushing me back against the wall, kissing me deeply. The press of her body and the sensation that produced on my nipples, the incredible softness of her lips and the taste of her lip gloss, her tongue exploring my mouth.
It was amazing and heady and dizzying! I was lost in it...
When she was done kissing me, she put her mouth up next to my ear and whispered “You have no idea how wet that made me…” I could only manage a small wordless sound.
Sarah reached under my skirt and again redefined the concept of “intimacy” for me. “Well, it seems like you enjoyed it too.” I could hear her wicked smile in her voice. I felt I might actually pass out.
I felt her hand push me against the wall and steady me. “Wait here sweetie…I will be right back.” she said softly.
I leaned against the wall, and gradually became reacquainted with my body. I realized I was quivering…I wasn’t cold, but I could not stop myself from shaking…my whole body was so…alive…my spirit so full of energy. I could not stop the tears that came next from the glorious sensation of it all.
After a few moments, I heard her step back into the curtained alcove. “You okay? ” she asked as I wiped fingers under the mask, still shaking. “Andy, tell me what’s wrong.” she said.
“No, I am fine..wonderful!...it’s just…so…much…good! Um…wow…” I managed shakily.
“I guess that means good?” she asked.
I nodded smiling weakly, but straightened up and tried to use my body language to tell her I was okay.
“Girl, if you thought that was good, just wait until you see what’s behind door #2!” she said with delight as she got behind me and propelled me through the curtain.
…………
I felt the final shackle click into place around my left wrist. I was now completely restrained, helpless, and completely at her mercy…
Well, I reflected, I had been completely at her mercy from the moment I walked through the door. She didn’t need shackles to bind me.
I realized that I was probably higher up than being on hands and knees on the floor. The surface felt softer and her position to me as she placed me in the harness felt like she was higher up.
“So pretty…” she murmured as I felt her walk around me. “But your hair is in your face and we can’t have that.” From the direction of the sound, I heard her go into her bedroom.
I moved slightly against the restraints, feeling their pull around neck, waist, and limbs. The weight of the breasts pulling against my chest as they hung down was delicious. Sarah had taken great delight in pinching each one again as she locked me in place. I tried to imagine how I must look in my little short pink dress, panties clearly showing from behind, the frilly socks and heels, hoop earrings and hair.
She returned and I felt her parting my hair and pulling on one side and then the other. What I suspected were bands went into place and I realized she was giving me two pony tails high on each side of my head. “You look –so- cute!” she exclaimed.
I felt her hand go along my back as she moved behind me. “I think you know what comes next, yes?” she said as she lifted my skirt to my backside. I felt her fingers probe my panties, taking them down to my knees.
“Did you use the douche like I asked you?” she said.
I nodded.
“Good girl…and did you put some lube up there too?”
I nodded again and heard her wicked voice say, “Good Girl! You smell very pretty and it’s important for a girl to be clean and ready for…whatever comes…“
I felt something soft and cold push up against the rosebud of my anus. It felt larger than the smooth dildo had a week earlier. I started to push a little back on it but she cautioned, “No, not yet…just hold there.” She moved it back into place, just pushing up against me. I shivered.
She moved again, this time to the front.
“I am going to take the blindfold off. Are you ready?” she asked.
I nodded. She did and with a flourish of delight as she stepped back out of line of the mirrors.
…………
There were mirrors…large mirrors to front, back, and sides. Large mirrors all reflecting me…
I looked into the eyes of a shocked girl with two high pony tails and hoop earrings. Sarah was silent but smiling as I took in the 360 panorama of…me.
I was restrained on a platform that stood about a foot and a half off the floor. It was covered in lavender satin and looked like it had pillows or something soft and poofy under it. The harness…well it was no longer just plain steel. It had been painted pink, but not just pink, but hot pink, and not just hot pink, but hot pink with glitter and there were little crystals winking from all over the collar and cuffs. The fucking machine sported a large hot pink very realistic shaped penis pushing right up against me.
As I turned back and forth the pony tails swished against the side of my neck and face. The dress, the shoes, the intense femininity and sexuality of it all…
I was…floored by it. A small sound escaped me…my mouth open.
Sarah moved a chair up, sat and asked eagerly “Do you like it?”
I nodded forgetting to close my mouth and kept looking at the girl…for certainly that was what she was…me…
“Yaaaayyyyy….” she exclaimed and fairly bounced in her chair clapping her hands.
I just kept looking, not able to take it all in. The effort this must have taken…the kindness…the acceptance.
The feeling was profound.
After a few moments, Sarah put her hand on my chin and moved my head to look at her.
“Well, here we are again.” she said smiling. “Last time, I did not know what to do with you. But now..I know exactly what I want to do.”
Her tone turned serious. “We are at another decision point, Andy.“
She reached behind her and produced the remote control for the fucking machine.
“I can let you out of here and you can walk…right now.”
She placed the remote under my left hand.
“Or you can push the button and let your new life begin…”
-Seven Days Earlier – 9 p.m.-
Sarah’s knock came exactly at nine. I of course knew she was coming as I had been peeking through the peep hole since about…oh seven…and pacing…and worrying.
Was she going to show up with the police and have me arrested? Or some boyfriend I did not know about and beat the shit out of me? I went over scenario after scenario in my head, but none of them really seemed to match what happened that afternoon and what I had seen in her eyes, her face.
None the less, I was flushed and shaking when I opened the door to her, managing a weak “Hi” and gesturing for her to come inside. She was dressed smartly in studded jeans and a flower print blouse that hung down over her hips in soft ruffles, her dark hair loose and flowing down her back.
I had taken a shower and was in chinos and a button up shirt. Seemed appropriate to meet whatever came that night clean and in the best clothing I could muster.
As she came in she held up a bottle of wine and two glasses, smiling and saying “I didn’t know if you drank wine or had glasses, but today seems to be a day for new experiences…soo….”
Her eyes lit over me and she frowned slightly “You look nice.” She said. I was not convinced either.
“Yea..uh…I mean Yes, so do you.” I stammered as we shared an awkward moment.
Finally I remembered myself “Uh…come in, let me take those.” She relinquished the bottle and glasses and swung a bag off her arm moving into the kitchen seating area.
“Here are your clothes.” She said putting the bag on my small kitchen table.
I said “Thanks…uh…” I pointed to the dress hanging on the door to my bedroom. “There is yours…”
She nodded and her eyes moved about my small apartment, taking it all in and murmuring “Nice place…” I wasn’t convinced either.
Looking at the wine, I said “I uh…don’t have a bottle opener.”
She made a gesture and said “Twist top. Only the best! ”
She turned and walked into my living room, looking around and picking small items up for examination.
“You uh…you want wine now?” I asked and she replied “Sure.”
I opened the bottle, poured out two glasses, and joined her in my small living room.
She took the glass from me and clinked it to mine. “Cheers…” she said, a sly look on her face.
“Cheers.” I replied simply and tasted the wine. I generally didn’t like wine, but smiled and made a yummy noise anyway.
She said “Thought it might take the edge off, so drink up sweetie.” And she plopped down on my couch.
I began “Sarah…I really am sorry fo-” She held up a hand and stopped me.
“No, we are not going to go there Andy, at least not yet.” She gestured “Sit.”
I sat. “Here it comes…” I thought.
Sarah looked around again and remarked “I imagined your place would be at least a little more feminine feeling…this is…very ‘guy’…and kind of ‘sanitized’.“
I groped for a response…”Well, um…yea, I am kind of living that way…” was all I managed.
“Why?” she asked frankly.
When I appeared lost again, she continued “I mean, transgendered people are not exactly mainstream yet, but Christ we have like six on campus, several are friends of mine, and my high school even had two people in transition….so, why not you too?”
“It’s a long story.” I replied stiffly.
She noted my tone and replied “Well, given what you did today, I think I deserve to hear that story, don’t you?”
After a few seconds, I reluctantly nodded, and haltingly began…”Not much to tell really.”
My parents both died of alcoholism when I was young. My dad when I was five, my mother at eleven. I was passed into foster care, where “fitting in” and “not making waves” was required if you wanted to stay with people. I was struggling with the experiences of living with an out of control adult from age 5 to 11 and it was all pretty tumultuous with the trauma of that AND the dysphoria I was feeling about my gender.
Sarah asked about some specifics, and I reluctantly shared. We talked for almost two hours.
“So…” she said when I had finished. “Not a lot of time or space to deal with feelings of being a girl?”
“No.” I replied and felt hot tears come. “Not…until the past two years…once I finally got on my own.”
She put her hand on mine and squeezed. “What about your parents…I mean, your foster parents? Don’t they know?” She asked.
I shook my head. “No. They….we don’t talk much...anymore.”
“Whooo….that’s heavy.” She said and was silent for a few moments.
She took another sip of her wine and asked “Have, or are you talking to anyone about all this? Any sort of counseling?”
I nodded. “I go twice a month. Because I was a ‘ward of the state’, they pay counseling fees until I am 25.”
“And, how much do you tell your counselor?” She asked. “Do they know that you are trans? Do you talk about that with them?”
I nodded. “Yea…”
She nodded back “Good. What are they telling you to do?”
I looked at the ceiling and sighed “They…she…is telling me that I should explore it…come to ‘grips with it’…stop…what she calls the ‘hide, deny, and repress’ mentality that I learned under foster care.”
Sarah nodded again and gestured. “Yea, looking your place I never would have guessed that you weren’t ‘just another guy’. Kinda’ wondered about what you told me earlier…”
“It’s, how I’ve learned to live…” I said.
“And now?” She asked. “This is an important moment in your life Andy…today changes things…it has to. Don’t you think?”
I blew my breath out. “Yea…probably…but…I don’t know…I don’t know how.”
She smiled and squeezed my hand again. “Well, for starters, we have to get you out of sneaking into girl’s bedrooms.”
I looked abashed and she continued with emphasis “By getting you your own bedroom filled with girl things…and the freedom and confidence to enjoy it.”
She stood and stretched, shaking off the heaviness of the past minutes. “Speaking of bedrooms, show me yours…and your girl things. I want to see what you have.”
As we passed into the hallway towards the bedroom, Sarah fingered her pink dress hanging on the door and said “You have an iron…good.”
She grabbed the dress down and spun on her heel, holding it up to me. I turned red and backed up a little but she moved with me holding the dress up to my body.
“You are a little taller, so it comes shorter on you, but it is a nice look. You should keep it...the panties too.” She said handing me the dress.
She turned back, opening the door to my bedroom and going in like she owned the place. She said over her shoulder “You will need them again I think.”
I stammered “Thanks…uh, what?” and followed her in.
My bedroom was one place that I felt safe enough to have some girl things out and I had left my pink comforter on the bed and a few items out even though an actual girl was coming over.
Sarah looked around “Now, this is a bit more like it.” She said running her finger over the coverlet and looking at the dark purple curtains covering the blinds.
She turned and reclined back on my bed and said in a sultry voice “So Andy…show me what you got…”
I turned beet red and I froze, my mind trying to determine what she meant.
Sarah giggled and said “Your clothes, Andy, show me your girl clothes.”
My closet contained just a few things I had ordered off the internet with what little money I had – skirts, blouses, rhinestone girl jeans, and two dresses. All of them were, to be honest, overtly feminine and I felt none of them fit me like they should. I pulled them out one at a time, and Sarah asked me to hold each up to my body.
When I was done, she asked quizzically “Is there a maid’s outfit in there somewhere too?”
I flushed and after a second, nodded. “Show me.” She said simply.
I reached into the far back recesses of the closet and produced said item. It was satin, black and pink and very short and very frilly. She gestured as I held it out and I put it up to my body, flushing in embarrassment.
She looked at me pointedly and said “There is no shame in that Andy. Christ I have a ‘fucking machine’ in my closet!” and laughed. I laughed too, and tension seemed to drain away.
She patted the bed. “Bring that over and sit down .”
I did and she took the outfit from me, removed it from the hanger and put it up against my sitting body, spreading the skirt out over my legs.
“You hold the top up.” She said as she sat back and regarded me.
I felt the soft cool satin and the lace as I held the bust to my chest feeling foolish and at the same time, liberated.
Sarah sat back and said softly “So…this is all at least a little sexual for you, isn’t it? I mean, why would you try out my fucking toy if it weren’t? Yes?”
I nodded slowly looking down at the shiny black and pink ruffles cascading over my pants.
“And, do you have fantasies about anal sex…sex with men? Sucking cock?” she continued.
I nodded again feeling flushed.
“There is no shame in that.” She said and I looked into her face and saw that she meant it.
“And what about women? Are you attracted to women?”
I nodded and said softly “Mostly I’m attracted to women really.“
“But you fantasize about guys too? Are you a woman in those fantasies?”
I nodded, glancing up to see her reaction. A soft sympathetic smile played across her face.
She considered for a moment and asked “If I could snap my fingers and make you female right now, would you do it?”
I looked up sharply and said firmly “Yes.”
She sighed and considered…at that moment, I actually wondered if maybe she could…
She turned back to me, very serious. “Will you explore being a girl with me, Andy? Is that something you want?”
My fears quailed, my limiting beliefs all clamored for attention, but my heart and my mouth instantly said “Yes.”
“You know what that means?” she asked. I shook my head “No...”
Sarah smiled. “Well, we can explore what it means together…”
Sarah took the maids outfit from me and laid it on the bed between us, then stood up motioning for me to stay.
She went to my dresser and pulled open drawers till she found panties, lingerie, which she inspected, closing the drawer. She turned back to me. “Makeup, jewelry?” she asked.
I pointed to my adjoining bathroom. She went in and I heard her opening drawers and rummaging. Clearly she found it as she came back out with a set of 4 inch gold hoop earrings.
These she held up to my ears, looking at my lobes and commenting “You should get your right ear pierced…these would look good on you.”
She set the earrings on the bed next to the maids outfit and gestured for me to stand up.
I…was so uncomfortable and turned on by this…all this…I was trembling. Sarah noticed, but did not do what I hoped she would do.
She took my hands in hers and said “We are both going to take a week to think on this.”
My disappointment showed clearly, but Sarah pursed her lips and nodded, leading me back out into the front room.
She stopped in front of the door and turned to me. “I need a week to plan things out, and you…you need a week to decide if this is –really- something you want. And if you want me to be an active part of.“ She put an emphasis on the word “active”.
“So you need to really give this serious consideration Andy. “ she stressed looking me directly in my eyes. “Do you understand?”
I nodded.
“I would like to begin next week…unless you put a note under my door saying ‘No’. That’s all I need, and we will never discuss this again.” She said. I visibly paled.
“If you decide you want this, then go get your ear pierced as a gesture to me that you are up for what we will do together…and remember, you are getting involved with a girl who has a fucking machine and a bondage harness. she said that last forcefully.
She looked up into my face and kissed my cheek. As she opened the door she got a wicked grin on her face and said “I am a dangerous girl with plans…you should be a little scared.“
And then she closed the door and was gone.
Her eyes were green, and they shone with intensity as I locked gazes with her…I pushed the button.
The fucking machine behind me sprang to life and a very realistic shaped hot pink penis pushed its way into me. My eyes went wide but still held hers as it opened me all the way to its most forward position, slightly painful. My hips rolled, repositioning to take the entire dildo as it came on and on into me, pushing relentlessly. It brought me just to the point of crying out before it began its slow reverse, and still I held her gaze.
I had spent the week planning to end my life, and begin a new one. I was absolutely terrified.
Sarah matched my gaze until the shaft retreated fully, and began its second deep thrust into me. Then she sat back and fanned her face with her hand.
“Wow Andy…you really know how to talk to a girl.” She said, flushed with excitement.
I was forced to look down and grunt as the second thrust took me. I felt her hand on my head.
“Yea, it’s a big one.” She said softly leaning forward and stroking my hair. “Take it, for me.”
I managed a nod and a glance up at her to see her smile.
“Good girl…” she said, and leaned in to kiss me.
She stroked my hair for a few more seconds as my body adjusted into being fucked with the large dildo.
Sarah stood, bent down and put her mouth next to my ear. “It’s going to gradually get faster…” she whispered.
She walked around me, touching me all over, tweaking a nipple on the breastforms and delighting in my jumping and shivering at her touch.
“Look up…look up and see yourself being fucked in the ass.” she said. “Look at the girl in those mirrors, that girl is you.”
My breath came in gasps, the intensity of the fucking…seeing myself in this way…deeply feminine and erotic sensations intertwined in me.
“You’ve been that girl ever since you were five and felt the difference. Felt the girl inside you that people didn’t want to see because you had a penis and you were supposed to be a boy.”
“But you weren’t Andy…you were a girl. And you knew you were a girl. You told me so.”
Sarah was walking around me as she spoke, her voice intense, her steps matching the slowly increasing pace of the dildo. I felt the pathway open like a flower and was rocked by a tremor of delight. My panties were wet, the sensation, delicious.
“Gender has nothing to do with what’s between your legs, or what clothes you wear. Your gender is determined by what is in your heart and your spirit. Your gender is what you feel and what you declare to the world that you are! Look at that girl! That girl is you!”
Another tremor and my breath came in shallow gasps as the penis rammed into me faster and faster. Sarah was moving quickly around and around me, touching me, kissing my cheeks, running her hands up the backs of my legs.
“You’ve lived by hiding her, denying her…hiding YOU and denying YOU! No more.”
The penis rammed home and withdrew faster and again faster and again faster.
“You are female because you feel female. You are drawn to female things, you think female thoughts. It is what is right for you at the core of your being. You are the girl, the girl is female and the female is you! Look at her!”
The girl inside me whispered “Yes…”
Tears came. Tremors intensified. Everything went faster and faster. I began to thrash and cry out uncontrollably.
“Answer me…are you a girl? Say it! Are you a girl?!”
Waves washed over me….her touch seemed everywhere…but the girl said firmly “Yes…”
“Louder! Declare her! Claim her! Are you a girl?!!”
The orgasm hit me like a typhoon. I was the girl who cried out “YES!” and then cried out again and again, wailing now, crying now as the sensations drifted down over what seemed to be an eternity.
And when it was done, Sarah moved quickly to release me from the machine, whispering encouraging words, caressing me with soft touches, and wrapping me in her arms as I cried.
Her head bent over me, her arms held me and smoothed my hair, she said softly “From this moment forward, you are a girl.”
The Lady with Red Hair
By Sabrina G. Langton
***
Just a quick little fictional account of a party I went to years and years ago. It was the early 90's and I updated it to sometime around now... Thanks for reading I hope YOU like it, F everyone else... Haha...
***
The Party
It was a beautiful day in L.A., but I had a feeling this was a bad idea.
I was inside the lobby of a huge apartment building in Beverly Hills waiting to be allowed up to the twenty-first floor. I had met another crossdresser on social media and she invited me to a party. I don't know why I said yes, the only place I go out dressed is to a mall and that is usually on Tuesday or Thursday afternoons when it's quiet. Very quiet.
I was waiting for the doorman to check for my name on a list. "That's Langhorn?" He asked me making me so nervous. My bangles on my arms were shaking, there was now a line of people behind me.
"No, I'm sorry it's Langton, Sabrina Langton," I told him in my little girl voice, I was trying to be soft and quiet. I didn't want the people behind me to remember my name.
"Oh, I see it, twenty-one, use that elevator over there." He pointed and I stepped over, sweating, finally off of a line.
The next bunch of people were pretty quick and the crowd was now next to me waiting for the elevator. The other elevator was deserted. I was glad I was dressed conservatively. I always tried to blend in, though I had a habit of wearing at least six-inch heels. My dress was black with pink, yellow and blue flowers on it. The hem dipped right below my knees showing off my nude pantyhose, but my black pumps made me higher than most of the people next to me. I was carrying a matching pocketbook and a shopping bag with three bottles of wine.
We all got on and I hid in the back clinking, thanking the Lord everyone got off before me, I didn't want to walk through the crowd, saying excuse me. There were only two other people left, a big tall man and another crossdresser. She was definitely a CD, she was big and tall herself with a long navy blue skirt, beige boots, and red hair past her small boobs. I looked at her in the mirror wondering if she could clock me as I checked my long pink nails.
I let them off at twenty-one and followed. I was about an hour and a half late to this party and I was a little relieved I wasn't the only one. I took a cab in case I had too much to drink.
Once we got to the door, I heard the music and the CD turned around and smiled at me. "Oh, hi you're going to Rain's party too." I shook my head. "First time?" I shook my head. "Get prepared to get a little wet." She laughed and winked at me as the door opened.
We were led into the big apartment filled with people and smoke, we pushed through a kitchen, and ended up in a huge gray room surrounded by windows and Downtown LA. Rain walked up to us, the sea of people parted for her. I have never seen her in person, she was a subscriber of my Instagram feed surprisingly, like I was hers, and she DM'd me to come to her party. I was flattered I had 70 followers, she had sixty thousand and was beautiful.
She almost kissed the three of us, "So you've met each other wonderful darlings, go get a drink and have fun. The bedrooms are that way." She pointed behind her past the crowd. She had long black pointy nails.
The other CD turned around, "Good luck, sweetie if you run into any trouble, and you will just ask someone to get 'The Lady with Red Hair,' or Dan. This is Dan." She pointed to the big man next to her.
"Hi, I'm Sabrina. I was hoping there would be more crossdressers here."
"Wait, are you not a real girl, wait are you?"
I smiled, I just turned twenty-seven, I was 5'8", not too thin, but nice and curvy and I passed quite well. I never had any trouble, people assumed I was another woman out and about. I just wished I could dress a little more sexy in real life and I should of today, the outfits at this party were crazy.
I smiled a huge smile, "No I'm just another crossdresser."
"Another beautiful crossdresser," She pressed the on switch on my dress with her finger and made me so happy. Dan seemed to be pretty ambivalent to the whole scene. "Go get a drink and mingle, try not to look so alone."
I dropped off the wine to the table and poured myself a red Solo cup full of Chardonnay and tried to navigate my way through the crowd. It seemed to me that the people here skewed a little older, maybe, their early forties to late sixties. A couple of men walked up and rubbed my ass but I walked away. I was nervous, I felt like I was going to pee.
There are three things I am so terrible at. One: I could never tell a person's age, I hated when someone asked me, I was always way off and usually they sauntered away in a huff. Two: I had absolutely no 'gaydar,' if that was even something people had, I was always told later and then I feigned surprise. Three: I was also a little confused about genders, I think I just didn't pay enough attention, I was always too busy looking out a window or checking in a mirror. Maybe I wasn't that nosy, maybe we should all wear nametags with pertinent information.
Mine would say: Twenty-seven, Bi crossdresser, Sometimes male, Looking for a view.
I walked around a little to check out the tchotchkes, Rain had a lot, but soon I got distracted again. I heard a keyboard, it was the eighties in the dining room. There was so much pot smoke, and water pipes littering the table. The long hallway looked like the streets of Manchester, England with women in short skirts and very high heels and the men in T-shirts. All with vapes. It smelled like a candy store. There is nothing sadder than watching women hold each other up for support, trying to walk in their non-platform heels on the carpet.
I watched a couple of naked people floating around, and a couple of men in leather and rubber from head to toe. I didn't like leather and rubber. I didn't really care much for pleather either. I should start my own club.
I wasn't used to this, in my head I was just another woman looking for love. Haha, I chuckled to myself. Love? I couldn't even find a bathroom.
Another two men surrounded me and started talking, they said I looked familiar but I knew they were lying. It was nice talking to men while I was in a dress, even though these two were so much older than me and a little drunk. One of them grabbed my free hand and brought it to his crotch. I didn't mind, at least I was mingling.
Suddenly a woman pulled me away taking my hand near the crotch and slightly tipping my drink. "The Lady with Red Hair asked me to get you away from those two." She gave the two men a dirty look and positioned me by one of the windows. I looked out thinking I should leave, but loving the view. I decided this was my new spot, right here, high above everyone in my heels. I could just make out my reflection in the glass, my figure looked pretty good, and I had my girlie stance down. I was posing in the reflection, I took a couple of selfies. I was making sultry faces at myself and winking. I would stay right here drinking wine and wishing I was at a different party.
When I had to seriously look for a bathroom I ended up in the middle of a couple of things I don't wish to remember. A man with a word on his face wanted me to walk on his balls with my high heels, and a woman wanted to squeeze my cheeks, with some kind of medical device. I stepped over numerous people fucking and sucking and then a CD with basketball-sized boobs squeezed my C cup breast forms. "You are way too small for me," She said disgusted and she walked away.
"Sorry?"
I then passed a man who was bleeding and he asked me to call him Daddy.
"Daddy, where's the bathroom?" He pointed.
I pushed through and finally found a toilet. Oh my god, I had to go, I was so nervous. I needed to get rid of the entire contents of the sixteen-ounce solo cup from my bladder. I locked the door, pulled down my pantyhose, and sat. I then looked to the side of me. There were three men in the shower in various stages of undress. One nodded to me and the others watched as they pushed their cocks against each other. I loudly tinkled. One of them put on the shower spray to drown me out. I finished, washed my hands, of course, wrestled a towel from the three men, and tried to make my way back to my window.
I then saw Rain, "Darling can you come here and do me a favor?"
"Okay," I told her as she led me deeper into her apartment. I walked past Batman and an Edvard Munch print. She led me into a dark, back bedroom. This didn't feel right. There were people there, a tall Spanish CD with a lot of makeup on and only a little bit of clothes. A Black man was sitting on the bed, ignoring me with a leer.
"Here you go," Rain said and closed the door. Thump.
The CD brought me over to the man. "I'm Little Timmy," he said. And then I saw his cock, he was anything but little. They made me sit next to him and they put my hand on his massive cock. Then the CD sat on a chair opposite and pulled out her own cock.
"Rub it, baby," Timmy told me so I did, I would make him come, get the hell out of here and then find some hand sanitizer, a lot of hand sanitizer. I wasn't used to being with men like this. Just because I flirted online with guys didn't mean I wasn't still an amateur with the male anatomy.
His cock was so big, my one hand with my long nails was doing nothing so he made me grab him with both like a baseball bat. I pumped and tried to swing his cock, he was wet and I was nervous he would get mad at me. He didn't look like a nice guy. He looked a little bored.
"Suck him bitch," The CD ordered. I looked at her, there was no way I was putting him in my mouth, he looked so unsanitary. Timmy grabbed the back of my head, I felt my wig shift. Then the CD got up and started rubbing my back, I felt her hard wet cock against my arm. My lips were hovering above Timmy's monster cock and his grip on my real hair was getting stronger, the CD now started holding me and pushing her cock harder against me. She was kind of sticky already. I was rocking and the black cock was hitting my chin. Timmy had such bad aim. I started to pee a little bit, my panties, dress and the bed were now wet.
Both the CD and Timmy were pushing me more onto his body, I was hunched over and could barely breathe, I wanted this to be over, how the hell did I even get in here. I just wanted to stretch. The door opened, I felt the two of them being pulled off of me, and a hand helped me up. It was Dan.
I stood up and in the doorway was The Lady with Red Hair. She said to the other two, "Go play with someone else, you two are fucking ridiculous." They both walked past Dan. The Spanish CD mimed to call her.
I wasn't upset, but a little more than embarrassed. "Thank you."
"Fix your wig before we go out." So I did, I looked terrible. I brushed my hair and painted my lips as she and Dan watched. I was ready to go, I was going to keep my crossdressing in the closet where it belonged. This was a bad idea.
"Me and Dan are leaving, I'm only good for an hour at one of Rain's parties. Do you need a ride?"
I did. We left and I stole a bottle of wine from the table. Ooh, and a handful of napkins.
***
Turns out they lived in Long Beach, not too far from the Queen Mary. Me, I was on the way to Lakewood.
"I'm Angela," The redhead told me. "I don't use my real name at any of Rain's parties," She laughed, and the both of us drank Merlot from the little cups I keep in my bag, while Dan drove. I sat on the napkins.
We talked the entire half-hour drive and I told her I wanted to start going out as a woman more. I was tired of being beautiful by myself, looking at my computer and hiding all day.
"Well going to Rain's was not the way to start, why don't you come over Saturday to our house. We can do regular normal everyday things, ha."
"Can I help with the laundry? I have a knack for folding."
She laughed, "Of course, but Dan doesn't let anybody touch his delicates but himself. Especially when he is wearing them."
***
They dropped me off. I liked them. Dan didn't say a word.
The back of my dress was still damp.
I wasn't kidding when I told her I would do her laundry, I just wanted to help. I was thankful for them and I would love just to be of any assistance they needed. I just wanted to dress up and be treated like a girl. It usually wasn't as easy as I thought.
The only thing that bothered me was that Angela looked like a man in a dress and they were both much older than me, maybe in their forties, early fifties, late sixties. I don't know. She had a pretty face but she wore just a little makeup. She was quite stocky and had no shape at all, even her boobs were small compared to her body. I was at least two cups size bigger than her. She also wasn't the best dresser either, not like I was any better, but I'm sure she didn't pass. The only thing about her I loved, was her hair. She had a long red-haired wig, it was very nice looking and probably expensive. I tried using my own strawberry blond hair but I almost always went out with a wig too.
I went over on Saturday.
I now see them every week, from morning until... well as late as they will have me. It was great meeting Dan and 'The Lady with Red Hair,' turns out she wasn't even wearing a wig, and she was a real live woman. Who would've guessed? I'm glad she didn't ask me to guess her age.
***
The End
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