Amy’s Return

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Amy’s ReturnThe phone screen displayed Amy’s name, I had not spoken with her in months, my curiosity piqued I took the call but let her speak first.”Hello Daddy” her voice low and sultry the way I taught her.”Hello Amy, I see that hunky basketball player dumped you.””Uh, what, how did you….huh?”Ah the youth, so predictable. But I suppose I was no smarter when I was her age, looking back on those times, yes, I was just as dumb. “Because I know you my dear, remember I was the one that taught you. You were always my favorite.” Trans girls like real girls love compliments and she was one of the special ones, worth all the effort.”Aww, thank you, I miss you, I…””Want to come over tonight” she wouldn’t have called if she didn’t “you can tell me all about the douchebag jock that broke your heart.””He was such a dick Daddy, I feel…used. But not like you taught me he..””He broke your heart, that’s the bad kind of used, I understand.””You always do, I…” her voice had the tone of an impending question, like she forgot I had already answered it for her. The youth, predictable and dumb. “Come over tonight, say seven, we’ll catch up. I need to get back to work, what do you say.””Ok Daddy, I want to see you, you still in the same apartment.””Indeed, you know where, see you around seven, and Amy, you know what to wear correct?””Underneath? Yes Daddy.””Good girl, see you tonight, hugs, kiss kiss.””Kisses, see you tonight Daddy.”And now I have something fun to do tonight. My cock is already hard thinking about Amy bobbing up and down on it. Amy too probably, that’s the reason for her call after all. A little background on Amy for this story. Amy’s real name is Stephen, I met her while she was midway through her freshman year at one of the local colleges. It was at on of the local overpriced stuffy coffee shops that hipsters hang out in to be seen, or something. I don’t usually patron these establishments but they had free wifi and I needed to get emails out asap. I was sitting at a table by the window when Stephen sat down at an adjacent table and pulled out a laptop, Mac of course, again predictable. I thought nothing of the person sitting with their back to my left until they leaned over into their bag to grab the power cord to their laptop. The movement drew my eye away from my screen and as the young lad leaned over his shirt pulled up to reveal a pink pair of panties poking out of the top of his jeans. This reminded me of my college days, revealing slight hints of feminine clothing to seduce and use men. Was this young lad as aggressive as I was in those days? The body language and accompanying clothing suggested not. Still, the pink fabric poking above the denim was enough, I wanted this beautiful creature, thin with neck length blonde hair in a no particular cut. I took a piece of paper and wrote “I like your panties,” I folded it and slipped it in front of the Mac. Stephen turned with eyes of confusion and a little shame. I winked wrote a second note quickly “You’re sexy, you should embrace that side.” Stephen took the note, thought and wrote back “What do you want?” “I returned the note, “You. Want to get some coffee to go? Chat somewhere private?” Stephen eyed me up and down, doing the standard mental calculations of is this guy a threat, dangerous, what happens next? I kept a slight smile on my face, winked again then nodded my head toward the door. Stephen took a moment then nodded and began to pack his laptop, I smiled and packed mine.Outside the shop I introduced myself, Stephen gave me his name but nothing else, shy and unsure of himself his body language betrayed inexperience and lack of self confidence. I knew it was best to do the talking, be upfront about everything and don’t waste time with minutia. I gave my my friendly smile, “I couldn’t resist writing the note after seeing your panties, they look very sexy.” Stephen looked questioning. “Your shirt lifted up when you reached into your bag. Like I said, I couldn’t resist wanting to know more about you. I used to crossdress when I was your age, I loved it. So I wanted to met you, seeing as how you share a similar interest I once had. Do you dress often?””Uh…no, I just fool around.” We continued down the street towards one of the smaller parks in town, Stephen followed, intrigued by this older man who discovered his secret fetish. “So your just experimenting on your own. Based on what you see and read on the internet. Masturbating in front of your computer, maybe on cam, fantasizing what it would be like to go all the way.” Stephen took a look of surprise and excitment. We entered the park and I nodded over to a small grove of trees. “I can honestly say I want you, I want to see you in nothing but those panties, and in more. I used to be like you and seduce older men, but no offence, you seem to be more of dreaming about it than doing it. I could teach you if you like, dress you, makeup, etiqueitte, personal safety. I can make you wanted by men.” Stephen was silent for a moment, then reached forward gently and massaged my cock through my pants. “Good girl.” Stephen’s sigh was audible.That night Stephen came over and I began seducing this young creature. Business was becoming tedious and I needed a distraction, so for vanity and ego I began turning Stephen into Amy. Over the next weeks I took my time, introducing her to the feminine arts. Amy took well to it. She shuddered with excitment when I put on her firs training bra. She pranced around the room when I gave her an innocent looking sundress. Her smile was bright when she saw her face in the mirror with blush and lipstick (it did take some time until she was able to this herself without smearing). High heels were a challenge at first so I told her to practice in her dorm room. I commanded her that when she was with me and was Amy she had to pee sitting down, blushing when I watched her tuzla escort to make her comply. I stroked her cock and made her cum, I could see the momentary shame in her eyes before succumbing to her desires again. She took to her cock sucking lessons hesitant at first then gobbling me down with enthusiasm. I trained her in safe recretional party favor use. By the time it came to her anal hygene lessons she was fully embracing her feminine sexuality. When I took her boy pussy for the first time I could tell she had changed, that she now wanted this, and I was only too glad to give it to her. She wanted to stay over more and more but I told her to spend some nights in her dorm, focusing on her studies. She dressed as boy in school but always with panties underneath. On the weekends we would spend nights together and occasionally I would invite my other trans friends over for her to practice with. The first time Amy penetrated anyone was my friend and former lover Tonya, after Amy came she sucked on Tonya’s cock for an hour in gratitude. I was beginning to think of Amy as more than a project, she had potential to be a true lover and partner in life. Dressed in an evening gown with high end heels and airbrushed makeup, Amy was trans sexuality weaponized, confident now and daring, seductress and slut. Then she left. “I met someone, he plays basketball at school. Thank you and I love you, but he is what I need.” C’est la vie, youth is wasted on the young. I will admit that this young man would be appealing to Amy, two triple doubles in the regular season and making the big dance in March. So yes, if I were Amy I would have fucked his brains out and don’t blame her for leaving. But that was beside the point, it was plan to time for Amy. Tonya and I had a hot fling a few years back and have always remained good friends in life. When she was having trouble finding a job as a trans girl who dressed full time she used her night school MBA and came to me with a business plan. In her conservatine business skirt she sat across from me on the hotel bed and asked for money to start an adult store. The dear girl was past middle age and wanted something for herself, her proffessionaly bounded plan proposed an adult store with a “private” arcade for a membership fee. The plan had all the diligence, including the local city council members she was blowing to get permits. Impressed I agreed not just out of friendship but for the VIP arcade which she had already virtually decorated with freeware. That night we made intense love. I fucked her for hours, a knowing lover she changed positions often, my cock throbbing inside her ass as she reached climax again. “Thank you daddy, for everything.” I said nothing as I gripped her tighter and increased the pace of my thrusts.Tonya’s store was not far away, hopefully she was working. Late afternoon and when I walked in Tonya was behind the register checking out an older woman who smiled as she took her bag and reset. “Take these” said Tonya adding a few disinfectant sample tubes to the bag, “enjoy but always keep it clean. The woman smiled again and blushed as she went by me out the door. “Well hello partner, what brings you?” Standing behind the counter was a late forties full time corssdresser in a short skirt and tank top. Her hair was done by her submissive, an asian boy ten years younger and another full time crossdresser. I walked over to her and we exchanged pecks on the cheek before she sat on the tall plush stool she kept behind the counter. “Amy called today.””Oooh, I see. What are you going to do?” “Still fantasizing. I’m going to need some items though. Nothing too off the bar though, what’s new and expensive?””Lot’s of items, been a while since you were here. Anything specific?””Just give me a basket, I’ll browse.”Tonya’s sub Sarah came from the back office taking off a pair of soft gloves. Sarah’s body was shorter than her mistress with a little wider hips, the unappealing canvas one piece jumper still couldn’t hide the way she swung them when she walked. Seeing me she approached with a smile. “Hello Sarah” I said giving her a quick squeeze around the waist. “Hello sir” she acknowledged by briefly pressing her face against my chest then walking over to her mistress. “Office is all set, Wonderland is clean, only 3 was a little nasty.””You wore your coveralls like I instructed?” “Yes Mistress, I did.” Tonya gave her a quick kiss a spank on the butt. A young man in his twenties walked in adopting an awkward slumped shoulder posture when he saw me speaking with Tonya. “She’s in 5” said Sarah pointing to the floor to ceiling prorn racks. The young man hurried to the non descript door behind those racks, a small sign above the door said “Wonderland.””Who’s back there?” I asked after the man was well behind the door.Tonya smiled, “Vivian.” “Oh, how nice, I’ll do some shopping now.” I browsed the store, choosing the toys and fetishes I intended to use on Amy. Finishing what I though would be enough I took them to the counter, Tonya and Sarah where both curious about the selection. “These for starters.” Tonya took a blister pack of anal beads and examined them. “I remember when you used these on me” she coupled with a soft sigh. “I like the brand, the size is appropriate. and the action is always good.” Sarah pawed the basket taking out a few items with oohs and aahs. “Also” I approached the glass counter and began to point “the collar, the chain and the plug.”Sarah motioned toward the larger dolphin shaped one but I corrected her, “the sparkly one, and a bottle of poppers cutie.” Sarah began boxing the items.”Shall I take this out of this month’s check?” Tonya had the items all laid out.”No I’ll pay cash, keep your records straight.””So” said Tonya holding up the box of handcuffs, “are you going to break her?” “Probably” I answered flatly.”That is so hot” came Sarah, rubbing tuzla escort bayan her nipples gently. “Are you sure you don’t wanting anything else?” Tonya’s sub opened her mouth and played around red lips with her fingers. She began swingeing her hips. Tonya gave her a stern look and held up a finger. Sarah stopped immediately, looked away, and u*********sly reached down to her panties. I took in the picture with appreciation. A willing sub being chastised by her mistress, u*********sly reaching down to their clit, trapped tight in a locked cage. Sarah closed her eyes with a face of discomfort, I could tell her little cock was swelling against the chastity device, just aching. Her only release anal stimulation and no one to give it to her. She shifted her weight from foot to foot, rubbing the cage through her skirt, helpless to find release.”I’ll see you girls later, if you leave Friday night open I have an idea.”Tonya smiled, “Can’t wait.” As I left she turned to Sarah, “just look at you…..sigh.”A few minutes before seven I had everything ready in my apartment. I stretched a little to limber up for the events to come. At seven came the knock on the door. When I opened the door I saw Amy wearing her boy clothes, tight jeans and a flannel shirt, but like I taught her both buttoned on the left, something the casual observer would miss but a tell to someone who knows what to look for. Emo style bangs hung around her temples, the slightest hint of eye shadow over her lids. I could tell she was nervous, she was coming home to her first Daddy after all, and she had not left on the best of terms.”Hello honey, come in.””Thank you” she said timidly.I put a hand around her waist and pulled her gently in to me. “Welcome honey, would you like to slip into something more comfortable?””Are you going to punish me Daddy? I know I wasn’t the …” she trailed off looking for the words.”A little bit, but you know me. I’m more interested in you. We’re going to spend more time fucking than anything else.” Her eyes showed excitment and hesitation. I kissed her. “Come into the bedroom, I want to see your body.” I lead her into the bedroom and kissed her again, “Undress.” Amy unbuttoned her shirt to reveal a blue and white bra, then she unzipped her jeans to reveal a matching set of panties, her little cock blossoming underneath. She stood with her hands by her side as I taught her while I ran my warm hands up and down her arms and legs, still cold from the walk over. The hormones she was taking made for two small buds underneath her bra, her legs were perfectly shaven, her butt was begining to slightly bubble from the estrogen. I slipped her panties down to examine her cock, always small it was shrinking a little more from the hormones but still hard. “Bend over.” Her cute little hole was shaved and looked tight, it hadn’t been used in a while. “Do you want to give yourself to Daddy?”She put her head on my chest and with a slight tremble in her voice said “Yes, please take me.””Let’s begin” I said and walked her over to the bed “lay down on your back, hands on the backboard.” I took out two silk ropes and began fastening restraints. Tying one of her hands to the post she arched her back in anticipation. I fastened the other to the opposite post and pulled both tight, spreading her arms. “The first thing I’m going to do to you is take away that cute little clitty of yours, you won’t need it for a couple days while you serve me.” The other rope I used to fasten her ankles to the bottom two posts. I adjusted both ropes so she was spread eagle in the middle of the bed. “Comfortable?””Yes Daddy.””Do you know what comes next?””I think so Daddy.”I took out the brand new CBT cage and opened it, letting her see all of it. “This is going on you, but look, you’re too excited for it to fit properly right now.” Her hard little slitty twitched in anticipation, I saw the bulb protrude above the uncut foreskin. The skin was tight, her excitment heightened by the anticipation of what was too come. I leaned over and gave her a kiss, stroking her hair and cheek. “Daddy’s going to give you your last orgasm for a while, let’s say 72 hours, if you’re a good little girl after that time I’ll take you back, understand?””Yes Daddy.””That’s my good girl.” I began with her clitty, stiff and straight, she moaned and arched her back. Amy arched her back and wiggle her hips as I moved towards her sack, caressing the dorsal nerve I felt her clitty pulse a bit, it was too soon for her to cum so I gently withdrew, Playing with her nipples while she looked into my eyes, that anticipation of release coupled with the slight fear of what would come after. I returned to stroking her clitty, dabbing the precum off the top. The technique is to do it ever so gently that she can’t reach orgasm, she tries to thrust her hips up, hoping for a harder grip but I do it ever softer, denying her satisfaction. After about twenty minutes I give her a kiss and remove a vibrator from the drawer next to the bed. I place my thumb and index finger on the side of her clitty shaft and massage the dorasal nerve with the vibrator. Increasing the vibration and grip she writhes in the restraints while I flick her girly sack with my pinky. When she clothes her eyes and gives a gutteral moan I maximize the vibration and stroke her shaft hard. Amy pulls against the restraints and gives a gutteral moan. I use my whole hand on her shaft and pin the vibrator just bellow her clitty’s bulbous head. Her shaft throbs as I grip tighter, she pulls on the ropes trying to contract into the fetal position. Then she climaxes, sissy juice pours from her clitty high into the air, landing on her little a-cup titties and stomach. I have seen her cum before but this intense, at least a full once, emptying her sissy sack. She goes limp, drained physically and with emotional release. Amy often goes to sleep escort tuzla after orgasm and this time is no different, she goes slack in the ropes, turns her head to the side and closes her eyes, in a few seconds she is softly snoring.I go to the bathroom and return with a damp washcloth and baby powder. While she snoozed sofltyI cleaned her chest and stomach. Then I cleaned and examined her clitty. It had gone completely soft, shrinking to a size barely larger than my ring finger. I peeld back the skin around her clitty head and wiped away her drying sissy juice, wiped carefully around the base and finally all around her little sissy purse noticing her boy balls had shrunk from the orgasm and hormones. Amy was beginning to stir, she pulled softly at one of the ankle ropes then her wrists, I knew she was awake but still had her eyes closed, still enjoying the post orgasm come down. I applied some of the baby powder around her clitty and sissy purse until it was soft and smooth. I reached for her caged, knowing she was awake now but still feigning sleep. Eyeballing the measurement, I knew it would have to be adjusted to its second smallest setting. Placing the circular base around her shaft and purse I tightened it snug to her. She took a breath but kept her eyes closed, sighing. I placed the pins in and secured the cage around the head of her clitty, with a secondary bar splitting her purse. I took a small, heart shaped silver lock from my pocket and placed it through the loop, securing Amy’s new cage in place. I gently tugged on it to make sure it was secure, it was tight enough not to fall or sag, but not to tight to cut off circulation. Perfect.I lay next to her, caressing her cheek, knowing she was awake. She pulled softly at the ropes, and nestled her cheek on my shoulder. “It’s done now, I’ve taken away your favorite little sissy toy, its all locked up.” She rubbed her cheeks on my chest, sighing. “Say thank you Daddy.””Thank you Daddy, this feels so much… so much..like…right.””Good girl, you were always my favorite little sissy.” I began loosening the ropes, sliding them off her wrists and ankles. “Come stand in front of the mirror, take a look at your cute little cage.” Amy stood in front of the mirror, looking at her cage, then to her eyes, then to mine, then back at the cage. I reached down and gave it a little giggle. She reached down and touched it, pulling on it, moving it from side to side. I put my arm around her and kissed her, she kissed my back, standing on her tippy toes to rub her caged against the hard cock in my pants. “Do more to me Daddy, please?””Yes, there’s more, you need to be plugged, then we can look at new outfits for you.” Kissing me again she said “thank you Daddy, I felt so lonely without you.” “There’s a disposable enema in the bathroom, let’s rinse your little pussy.””Could I have a cigarette?” she said with begging eyes.”Of course, for being a good girl and accepting your cage. We moved to the bathroom where I opened the window and retrived a pack of smokes. I watched her light one as she stood naked in front of the mirror, contemplating the meaning of what had just been done to her. occasionally reaching down to examine the trap her genitals had just been placed in. I handed her the disposable and like a seasoned slut got down on all fours, face down, hips up, reaching back to insert it. “Here let me help you.” I licked my fingers and rubbed them on her pussy, I could feel it clench to my touch. Inserting the tip slowly, giving a slight circular motion, I slid it down until the nozzle was fully in. Amy sighed and took another pull off her cigarete. I slowly squeezed letting the saline solution fill her up. I carefully remove the disposable and threw it away. “Now wait a few minutes.””Yes Daddy, I know.” She took another drag of her cigarette, slowly rocking her hips from side to side. I lit one of my own and enjoyed the view, my little sissy girl on my bathroom floor with a pussy full of saline, locked and submissive to her Daddy. I beautiful sight. Her pussy clenched, trying hard to hold in the solution. She looked back and wimpered. I nodded and helped her up and over to the toilet. With an axhale came a whoosh as the solution landed in the toilet. She sighed, taking another drag. “I cleaned before I came so I should be good Daddy.” I handed her a baby wipe which she used to wipe away the excess, then tossing in the toilet after taking the last drag of her cigarette. “Now for your plug sweetie.””Yes Daddy.””Stand in front of the sink mirror, lean slightly over and place your hands on the counter.” Amy complied obediently and I left to grab her plug. I had left in the refrigerator, I wanted it to be cold when I inserted it. When I came back Amy was bending slightly over like she had been told, swaying her hips and blowing soft kisses to herself in the mirror. I stood behind her, put my hand around her waist and leaned in for a kiss. I placed the cold metal plug on one of her nipples, she shudderd and hunched her shoulders but didn’t take her hands off the sink. She still remembered obedience I thought. I knelt down behind her and spread her bulbous little but cheeks. Her puss was shaved and clean, slightly loose from the enema and previous toying but still tight. Taking a little KY in my fingers I slowly massaged around her pussy, feeling it relax and dilate. She moaned, Her pussy accepted my fingers easily, a small circular motion loosening it even more. Withdrawing my fingers I placed the cold metal plud against her moist pussy, it instantly clenched shut from the temperature change and Amy let out a gasp. I wiggled it a little and then pushed it in, her pussy clenched, then released and the bulb was in leaving the just the jeweled circular stopper snug between her cheeks. I stood and took her hands off the counter placing them around my waist, “Now your my little sissy girl Amy, how do you feel?””Thank you Daddy, just thank you.”For the next three days she wore her cage and plug dutifully, dedicating herself happily to her master. I’ll tell you all about that later.

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