A story about a crossdresser who finds a real cock for his very first experience with another person.
This story is for adult readers only, and not for minors. As such you the reader must be advised that it contains explicit sexual descriptions of Gay sex. IF YOU ARE NOT OF LEGAL AGE TO BE READING THIS STORY OR IF YOU FIND SUCH MATERIAL OFFENSIVE, PLEASE LEAVE NOW.
This is the work of a fertile mind. It remains the copyright property of the author and therefore you may not be reproduced in any way without their express permission. It is fiction, therefore similarities between characters and real people are unexpected and unintentional. If you recognise yourself or anyone you know. Please contact me immediately so I can change any future chapters.
I have received complaints about my habit of changing the way I tell a story. I tend to swap between the 1st, 2nd, and 3rd person’s perspective. My bad. They say it is harder to follow the action (understandable), for these poor individuals I am trying out a new technique. See if you can spot it, if you do, please comment. Let me know if it helps with the flow of the story. I draft these stories to excite and entertain the reader. The last thing that I want to happen is for a reader to be trying to work out who is saying what, at an inopportune moment.
If gay sex, or sex between males offends, do not bother reading any further. For those that do like the pleasure that only another man can give, then please read on. I try to write sex scenes with lots of details; I like to get my readers off. So, either slip your headphones on, or put your ear buds in, take hold of yourself, and listen to the tale of a chance encounter.
LOST
This is a tale that happened, not every precise detail, but it is as best as I can remember it. First, let me give you a little background. It is the late eighties. I was 23 I had just moved into my first home, a one-bedroom council apartment. Yes, it was small, but it was warm, dry, and the rent was cheap. Best of all, I could finally do whatever I wanted to, be who I wanted to be.
Which just happened to be dressing up in women’s clothing, I could finally be the girl I have dreamed of being. I still had to be careful with blinds and curtains because there are fifteen apartments in the complex, some overlook my unit. Back then I had acuminated quite a good lingerie collection. Bra’s, panties, bodysuits, several corsets one was cup-less, few different coloured frilly garter belts, a black boned waist-clincher. For the latter I have six clip-on suspender straps, and I was always buying stockings. There were also a red lace and satin nightie, the lace covers everything above my ribcage and the satin spills down around my knees. Sadly, back then I only had two dresses; it was a lot harder before the internet. It took guts to walk into a women’s clothing store and buy something. Lingerie stores were a snap, when asked I just said that I was looking for a birthday present. Worked a treat they would even gift wrap it for me. I was like a giddy 16-year-old when I opened my presents in the privacy of my flat. I became quite adept at shoplifting too, the old five finger discount method of shopping. Acquiring all my costume jewellery, Clip-on earrings, and a couple of gold-plated bracelets. Several G-string leotards along with other sexy lingerie store goodies, a little bit of make-up (eyeshadow, blusher, mascara, eye liner, and a few lipsticks), even though I never did caught shoplifting, thank God. I used to imagine that if I did get in trouble, I would offer to suck them and let them fuck my sissy ass, if they let me go. Shoes were a complete nightmare, although I did manage to find a warehouse sale and snagged myself two pairs of kitten heels. The old lady stocking shelves smiled at me when she busted me trying a black pair on. Grabbing another blue pair, I scurried off paying for them and leaving as quickly as my shaking legs would carry me.
Out of my two complete outfits my favourite by far, is my black long sleeve top, and the black ankle length skirt. The top buttons up the front with tiny silver buttons sixteen in total, they join the patterned panels in the centre with another four buttons at each wrist. The top’s made from cotton; it is quite soft and fits surprisingly well considering the outfit was a chance purchase. The skirt and top were matched hanging on the rack near the front of a women’s clothing store. As my fingers touched the flimsy hem of the skirt, a shiver ran down my spine. Quickly flicking through the rack, I picked out a size 12. Taking the garment to the counter, I used my trusty excuse.
“It’s, for my girlfriend.”
While paying the shop assistant, I was thinking.
“This’ll look good, I’ll tuck the top into the skirt then that elastic belt can hold it all nicely.”
I had found the belt in a car boot sale the previous weekend, another purchase for my imaginary girlfriend. It is two inches wide and has a gold clasp that clips into itself forming a pair of arrows pointing inwards. Its elasticity means it fits snugly around my waist, making the transition seamless. I have modified the skirt, I have removed the lining, now under bright light. i.e. under flash photography the skirt becomes transparent. I found this out by using a tripod and camera with a self-timer, (yes, before digital, it was the early 90s). I would take a roll of pictures and send them to a private developing company; I could squeeze twenty-seven photos onto a roll of film meant for twenty-four. They would send back the photos in the mail once they sent me doubles of half of my photos. Struck me as strange, then I thought about it a bit more. I realised there is someone out there that has naughty photos of me. I was not angry on the contrary it made me hard as all fuck.
I went through the photos finding which were missing, there were seven in all. Several that showed my made-up face, one full body length wearing my favourite skirt and top smiling for the camera. Underneath the flimsy skirt and clearly visible are my black lace top stockings. My suspender straps run from the stockings over my white thighs before diving under the six to eight inches of lining I had not removed from the skirt. My lace covered camel toe hiding my perfectly tucked clitty, the cotton top swells over my stuffed B-cup bra.
The second missing double is a close-up of me from the waist up, after I had taken my soft cotton top off. The lace bodysuit hugs my girlish body, the thin black straps riding over my slender shoulders, the bulging cups hiding their stuffing secret. Again, I am smiling at the camera. My dark eyeshadow, mascara, eyeliner, and bright red lipstick clear in the close-up. My long blonde wig flowing around my shoulders, a pair of heart shaped earrings hanging half hidden by my long ash-blonde hair.
The third showed me from the side looking over at the camera. My curvy white butt has a vintage vacuum cleaner handle buried several inches inside. The G-string bodysuit pulled aside; my cute butt dimples showing just under where the lacey bodysuit flares out over my hip. There is a wicked smile on my painted lips.
Another was a front view of me from my stocking tops up to my chest. My gloved hands splayed on either thigh, framing my tucked boi clit. The photo was that good I could see through the sheer nylon, the little tuft of red pubic hair between the swelling where my sissy balls hide inside my body. I had left the little tuft last time I had shaved before taking the photos.
A wicked thought crossed my mind. You see back then before the internet hooking up was a lot harder and could be dangerous too. As a porn addict, I had found a few publications that had personal adds. Ribald, Searchlight, Rosie but my favourite was Rosie Bizarre. It catered to a kinkier type of reader; each month they published a story from a reader. All you had to do was write a bit about yourself, a short bio, add in a saucy tale, attach a few photos which they promised to return. If the editor thought their readers would like it, they would publish. In the back of the magazine were the personals they were free to post, they got their money by charging $5 for each reply, quite reasonable and lucrative. Numbers edited down to maximize replies.
Finally deciding to take the big step I had built up my courage, I spent a week or more writing and then rewriting my story. I had already picked the photos, the four I described. If they good enough for the developer to steal them the editor at Rosie Bizarre will like them enough to put them in the magazine. The story was complete fiction about how I had lost my Dom, a neighbour, I was now looking for a new Daddy. The only true part was that I did want a Daddy figure to take control of me, and I had a crush on my elderly neighbour when I was 18. It had been a constant fantasy for me as long as I could remember. So, in the same envelope I included a personal add, ‘Sissy boi needs Daddy figure teach him how to be a good gurl.’ I deliberately mis-spelt girl to signify the fact I am a boy, but I want to look like and treated like a girl. A Dom would intuitively know I am a sissy fucktoy, who is looking to be an owned sissy again.
Every day after I posted the letter off to the Rosie’s editor. I would start the day with a hot shower including a power enema. I unscrew the shower head from its hose; I fill my bowels overflowing using the water pressure half a dozen times. After cleaning up and finishing my shower it is off to the bedroom. I have been wanking myself silly, fucking myself with a very flexible anal probe, a huge thick vibrating dildo or one of my other toys. One hand would only go three quarters of the way around the big dildo. The big fake balls are a good nine inches from the pointed head. I would kneel on my bed lube up my boi cunt fingering my slutty fuck hole. First just one finger then two as I open a third joins them. Picking up the dildo I would rub lube over the silicone, another squirt over the head. Slowly pushing it into my shitter, purring, and grinding back against the invader. Changing position, I crouch over the dildo line it up against my slippery boi cunt. Sliding down onto to the thick fake monster cock. My ass can take it easily because I have been using an inflatable butt plug to stretch my fuckhole. Dropping the dildo quickly replacing it with the butt plug its two-inch girth slides in with ease. Gripping the bulb, I give it four good squeezes. The plug inflates inside me, I feel the pressure against my sphincter, another two pumps on the blub. The butt plug is now three times the size it was before it entered my ass. My poor stretched ass hole cannot take it, giving up its battle, finally relaxing. The plug flops onto the bed between my spread knees. My slutty boi cunt gapes obscenely.
I did not expect my ad and bio with photos, to be in the next edition of Rosie Bizarre. So was not too disappointed when it was not. Over the six weeks it took for the next issue of Rosie Bizarre to hit the stands. My anal play had been out of control; I would bend my ribbed anal robe in half and shove it into my greedy fuckhole loving the stretch it gave me. I managed to insert an icy 12oz Coke can, after a few trial runs, I am now able to get the whole can inside. My sphincter closes and the cold can has disappeared; it is a fantastic and highly erotic way of cooling down on a sweltering day. Soon I upgraded and moved on to using a 20oz Coke bottle. I have had four pool balls clunking around inside of me a couple of times. They are a lot harder to keep inside but great for clenching exercise. Zucchinni’s are a permanent item on my shopping list.
Okay, to answer the critical issue, I hear you all want to know the answer to, well it is a big, huge yes of course. I have fist fucked my sissy boi cunt many times. It is not easy, but it is manageable. You cannot get very deep, you are lucky if you can get your whole hand inside, it is a real workout for your wrist, those hand dildos are hopeless. Once you have had a real hand moving inside your ass, feeling it go deeper or as it closes into a fist inside you. You will be just like me, a dedicated anal whore, the sort of slut that is addicted to having your sphincter stretched. The exquisite pleasure of feeling so full as they saw their arm in and out of your willing body. Anyway, I am diverging from my story. I may write about those experiences in another chapter.
Finally, the visit to the adult bookstore was fruitful. The newest edition of Rosie Bizarre was in stock. You had to be quick to get a copy. My heart was racing as I sat in my car and took the small 6”X8” glossy magazine from the brown paper bag. Quickly flicking through the glossy pages, suddenly there I was on page 15. Emblazoned across the top of the page four simple capital letters, LOST. The editor placed the story over three pages, one of my photos filling parts of each one. On the first there I was in my favourite skirt and top, leaning back showing my stocking clad thighs. The photo filled one side of the page, the writing flowing around the edge of the photo. Opposite on page 16 they had the waist up photo, and on page 17 there was a picture of me looking over my shoulder at the camera the old Hoover handle in my butt. It pissed me off that they had blacked out my face, I was willing for them to print my face. I supposed it was for legal reasons which is fair enough. When my photos finally came back four months later, I managed to clean off the marker quite easily. My cock was so hard as I read my bullshit story, my cock dribbled precum. They had published it word for word; a large wet spot appeared in my jeans. Quickly flipping to the ads, there it was black and white for everyone to see. ‘Sissy boi needs Daddy figure teach him how to be a good gurl.’ I blew my nut, filling the red silk high cut panties I wore that day.
I received over two dozen replies to the ad, sadly 99% were creepy, and a few were downright fucking scary. I was starting to have second thoughts until opening a letter from a man, he had signed it Master Shepard. That was the moment my life changed. His letter went on to say that he was in his late fifties; he worked in the legal profession. The photo he had included was of a fit quite attractive man, I was surprised he had included it his brown hair cropped short, greying at the temples. A nice square jaw signifying and enhancing his power, coupled with his delicious dad’s body, a hint of greying chest hair showing through the open shirt he wore in the photo. What he was looking for was not a toyboy or a casual fling; he was interested in having someone like me, I would do whatever he told me. Someone that he could meld into his personal living sex toy. The right person would, when summoned visit his office on occasions. If I were interested, I would include my phone number with my reply. He included a stamped self-addressed envelope, Master Shepard, and a post office box number. Cell phones back then were still new; most were the size of a brick, cost a fortune and only made phone calls.
My return letter was short and straight to the point more a note, rather than a letter.
Dear Master Shepard,
Greetings from your newest perspective sissy boi. My name is Sean but please call me Suzie. You can call me any time on 02*##*##**.
Could you please call me so we can talk a little before arranging a face-to-face meeting?
Two days later I was sitting on my sofa when the phone rang, my heart skipped a beat, was it him? It had been doing that every time the telephone rang since I sent the letter.
: “Hello Shawn speaking.
: “Hi Suzie,,,,,
: “Oh, it’s you. Um, hi Master Shepard. It is so nice to hear your voice.
:”You may call me by my given name for now Susie; you may call me John. Now, Suzie, I want to see you today. Tell me where we can meet. And who knows if we hit it off, and I want it to go further, I will pay for a motel room where you will call me Daddy or Sir.
:”Do you know where Heathlands bowling club is? I can meet you in the car park at 1pm this afternoon, John.
:”That sounds like a perfect plan, Suzie. How will I recognize my toy?
: “I’ll park on the outer ring; there’s always free spots out there during the week. I will be the blonde guy sitting in a blue Toyota Corolla hatch-back, shaking with anticipation.
:”Okay toy, I look forward to seeing you. Wear something sexy for your Daddy. Do not be late. Until this afternoon, Suzie.
:”Yes, John. Goodbye.
Hanging the phone back on its cradle. I could not believe what I had just agreed to. Were some of my wilder fantasies about to become reality? Could this man I know nothing about John Shepherd be the one. The one that would finally see the real me? The one that could unlock that door. I have just agreed to meet him, so I have taken the hardest step. It should be easier from here. A mix of trepidation, anxiety, and excitement filled me while I waited for 1pm to come around. After packing my favourite outfit, a brand-new pair of black lace-top stay-up stockings, a slutty red bra and panties set, my ash-blonde wig. Along with my make-up bag (1 eye liner pencil, 1 tube of mascara, 2 eyeshadow packs, 1 was shades of green, the other shades pink, a salmon pink blusher pack, three lipsticks, red, burgundy, and pink). Along with my black kitten heels and elastic belt, I put them into a sports bag. I wanted to show him that I was ready and prepared if he wanted to take things further. Before I left home, I had changed out of the white bra and panties I had put on this morning, into a satin and lace lilac camisole with matching French cut knickers. My dark shirt hides the lingerie well but with a quick flick I can pop the press-studs holding it together, revealing the sexy pale purple satin.
Arriving early, I parked where I told John I would be waiting. I was sitting in my Hatchback fingers nervously tapping the steering wheel. I saw a man, he looked like the man in the photo, he was walking towards me. It was him, the guy in the photo; it is John Shepherd. I could not believe it. This is the man I talked to on the telephone.
“This meeting is going to happen,” I said to myself. My, smooth cock started reacting to my aroused state.
He stopped beside the window of my Hatchback; his sizeable lump inches from my face. Looking down at me
:”Hello are you, Sean?”
My heart skipped several beats; my voice caught my throat.
:”Um yes. Hi. It is nice to meet you, John, right?
He simply nodded but did not say anything. So, as is my habit, I nervously continued. “I’m sorry, I was being careful, and it’s Susie actually. Your little slut, Susie, hopefully Daddy.
:”We will see about that. Was that story in Rosie yours?”
I did not think I answered as if I was on autopilot.
:”Yes, I sent it in with the advert you answered.”
:”Nice pictures, now do you have any experience as a sub?”
:”Thank you, I have more at home. As far as submissive experience goes it is telling myself to do things like, to suck on a dildo. So, no, not really, no I do not, but I am very willing to learn everything I need to know. I know I must obey your orders. That’s why I wore this.”
Grasping the lapel of my shirt quickly tugging it aside, three quarters of the press studs give way. The shirt drapes open to my waist revealing the gorgeous lilac satin and lace camisole hidden underneath.
:”I’m wearing the matching panties for you to Sir.”
His eyebrows twitched, rose a miniscule amount for only a fraction of a second; instantly his face settled back into a neutral expression.
:”Have you brought other clothes with you too, Susie?”
:”Yes, Sir, I can be that girl in the magazine, only I will be wearing different lingerie. Or I can leave what I have on if you prefer.”
:”Go to the Motor Inn Motel at the end of the interstate. Park in the shopping Centre carpark across the street from it. I am going to get us a room. You will drive straight there; you will meet me in that carpark. You know the one I am talking about, don’t you?”
My heart was racing; my palms were sweaty. I knew the Motel he talked about; I had driven past it many times. It was only a few suburbs away, the fact that most of the Motel’s clients were interstate travelling salespeople or business reps would alley any suspicions. John had picked it well; it showed he had put some thought into our initial meeting either that or I was not the first person he had taken there.
:”Yes, Sir I know the Motel, I’ll drive straight there now, and I’ll be waiting in the carpark for you.”
He did not say anything; he knew he did not have to. He knew I would meet him, that I would be there; he could sense it. My need for a strong guiding hand was evident in every action my submissiveness shone through.
Twenty-five minutes later I sat in the passenger seat of his Mercedes as we drove into the Motel. He parked in front of a row of rooms, grabbing my bag from the trunk John carried for me. Opening the door, he placed a hand in the small of my back as he ushered me through the doorway. It was if he thought I might run away, later much, much later I would come to recognize that type of gesture as a possessive reinforcement move employed by many Domms’. Stepping inside the room it was cool, a relief from the heat outside John had switched the air con on. It was your typical 80’s Motel room, a queen size bed with a tacky green bed spread. A pair of bedside drawers attached to either side. On the wall opposite the bed was a long bench with a small bar refrigerator tucked underneath. Sitting on the bench above the refrigerator was a tray with tea, coffee, sugar, and an electric kettle.
John dropped my bag on the bench, closed the door, and turned to me.
:”Show me your sexy lingerie. I want to see those matching panties you teased me with you little hussy.”
“Yes Sir,”
:”I wasn’t asking.”
He stepped towards me; only an inch or two separated us. His eyes piercing my soul; all I could smell was a combination of Old Spice after shave and mint. His eyes never left mine as he reached for me. In a flash, his large hands were gripping the lapels of my shirt. Quickly ripping the shirt open, he expertly flicked the lapels up baring my shoulders, before expertly trapping my arms beside and behind me. Stepping back, he admired my camisole clad body. Running a finger along the thin lilac strap of the camisole as it crossed my collarbone. His touch made me shiver and sharply draw in a breath.
:”Mmmmmm beautiful I like your taste; this colour suits you, Susie.”
With my arms trapped in my shirt, his hands roamed across the satin camisole. He twisted my nipples through the thin satin, bringing groans from me. Pulling me close, he forcibly kissed me. It was a kiss that claimed me, not a sweet I love you sort of kiss, no it was a full on ‘I fucking own you bitch’, type of kiss. Melting into his arms I open my mouth in surrender; our tongues spar, they fight a mighty battle, jousting like medieval knights. As we part, I playfully suck on his retreating tongue, a string of saliva still joining our lips for a second or two before he released me. Taking a step backwards I looked up at him smiling coyly.
:”Didn’t you say, you want to see my panties, Daddy?”
:”You’d better believe it. Drop those pants. I want to see your purple undies.”
I practically ripped off my pants, for the first time in my life here I was, me Sean dressed in my lingerie standing proudly in front of another person not a mirror. Posing, my legs slightly parted my tucked boi-clit hidden, now just a feminine curve in the lilac satin shimmering under the harsh fluorescent lighting. He looked at me with a burning in his eyes. It was the look of hunger, a wanting look, not a casual glance a longing look of desire. The look of a man who knew he had the upper hand; he is prepared to use his position of power to satisfy his needs. I nearly creamed myself in the satin panties.
:”Very pretty, I am going to have a quick shower, then you can have the bathroom, Susie. You can shower and make yourself pretty. You mentioned that you brought some red lingerie along too. Only sluts wear red lingerie, that is perfect for you, isn’t it Slut?”
:”Yes, Daddy red lingerie it is. Please try not to rip it, Daddy. They were very expensive.”
Again, my voice came out as if someone else was talking though me. This was a fantasy coming true, this man just called me a slut. I did not bat an eyelid; I just took it; I knew that it was true. I was here for one reason; I was here so John could fuck me; he had paid for our motel room and now it is my turn to reimburse him my fair share.
:”Well, you better fucking do as your told Bitch. Otherwise, they’ll be in tatters around your feet.”
His last couple of words dripped with menace and power; they told me that he was serious. Turning, he strode towards the open bathroom door. I quickly called out after him in the feminine voice, I had practiced and became quite good at, not to highly pitched, it has a sultry tone.
:”Yes Daddy, I’m sorry, I’ll be a good little girl for you Daddy.”
He did not answer, just closed the door. Less than ten minutes pass, the bathroom door opens, John walks out with a towel wrapped around his waist. A few beads of water still clinging to the dusting of grey hairs covering his chest. His brown, slightly greying hair at the temples; he is the picture-perfect Daddy. Look in the dictionary there is a picture John, just out of the shower glistening like a God, of him right under the definition. I was right about his dad’s body he had the physique of a much younger man. From his nicely defined muscles I could tell that he spends time at the gym. My only reservation was could he cum more than once, God, I hoped so, or he might have to investigate getting some Viagra. Hooking a thumb gesturing towards the vacant bathroom.
:”It is all yours Little Lady, do not keep me waiting too long. I’ll come in and get you if I must.”
Grabbing my bag, I head into the bathroom.
:”I’ll be as quick as I can Daddy, it takes time for a girl to make themself pretty for their Daddy.”
I quickly closed the door, I did not wait for his answer. It was my little way of being defiant, playful, I was not a stranger to painful punishment. So far, it has all been self-inflicted punishments. Encircling my hairless balls between my thumb and pointer finger then vigorously flapping my balls up and down. Slapping them hard against my hand or down onto the stiff nylon bristles of a hairbrush. I regularly smack my trusted balls or the squeezed knob of my shaved cock with a riding crop. Mine has an extra-large leather flapper on the end. It is delightful the way it slaps my trussed balls, making them swing in the edging ring meant for a man’s cock that I squeeze my smooth hairless balls through. The slapping yet painful it does something else; it sends sparks of pleasure coursing throughout my body. The slapping of the leather against my tender nut sack is music to my ears. Since it was our first meeting, I had not brought my riding crop along. Next time I most definitely would.
It took me a full twenty-five minutes before I stepped out of the bathroom. My favourite dress the lilac lingerie a pair of lace top sheer black stay-up stockings. My ash-blonde Jennifer Aniston wig on make-up applied mascara, purple eyeshadow, and burgundy lipstick. Around my neck was a four-inch-wide dog collar one of my friends had made for my mom’s dog. It was not big enough for the mutt, I grabbed it telling her I would give it back to my friend. Ha! Yes, sure I did. I took it back to my flat glued some suede inside it as a lining. It fits like it me as if my friend made it for me. The buckle hidden under my hair and sitting under my chin is the “D” ring where John can attach my leash.
John sat in the only chair in the room wearing nothing but a small white pouch like a jockstrap, his impressive bulge front and centre. When he saw me exiting the bathroom he stood, picked up an extremely expensive looking camera, and proceeded to take several photos of me. He directed my actions telling me to slowly peel off each item of clothing. All the while saying that the camera loved me and that I was pretty, dumb me fell for every word.
:”I like the collar Susie, it suits you. I have brought along a special toy, and because though you are a slutty sissy, you are going to take for me. Aren’t you Susie?”
I had no idea what toy he was talking about, but I agreed to take it as he had put it.
:”Yes, Daddy, whatever you say.”
I stood there in my stockings, black kitten heels, lilac camisole, and high cut panties. While John rummaged around in the large duffle bag he had brought in while I was in the bathroom. From it he produced the largest butt plug I have ever seen to date. I mean it was fucking enormous, although it was intimidating, for him I was willing to try. I estimate the diameter to have been between five and six inches at the widest point narrowing to a manageable two inches once it was fully seated.
At first, I struggled but with lots of lube and perseverance, (physically pulling myself open) with a final shove the enormous bulb won the fight against my sphincter. As soon as the widest part entered my asshole my sphincter snapped down forcing the butt-plug deeper. It hurt and I had to wiggle around to stop the pain I was feeling from the massive plastic invader poking into my upper bowel.
:”That’s a good gurl Susie, you like Daddy’s plug don’t you Sissy Boi?”
:”Oh, fuck yes Daddy, it is so big though. I didn’t think I’d get it in for a minute there.”
He gently caressed my upturned plugged butt, leaning down John lifted a black leather harness from the duffel bag. Placing the largest, a two-inch-wide strap, around my waist buckling it tight. Next, he pulled a pair of smaller straps from behind my back, down over the butt-plug. Feeling him snapping four press-studs onto the plugs wide base, I realised that he was making it near impossible for me to remove the plug without his help. My cock twitched at the thought, or it might have been because John was busy threading the thin straps though a weird type of cockring.
It was an ordinary inch and a half diameter ring but there were two small eyelets welded at 90 degrees to the ring, perfect for the leather straps. As John pulled the straps tight, he guided my dick through the ring, sliding the cool metal down to the base of my hairless shaft. The sensation a sharp grounding focus, the blood pumps into my dick as John starts pulling my smooth scrotum up through the shiny ring. He worked meticulously drawing the skin upwards, I can feel my ball sack cinching trapping my nuts with nowhere to go.
:”Breathe Susie, breathe for Daddy.”
As I take a breath John, placed his thumb against the bulge and pushing against it, popping my balls up into my groin, quickly pulling the rest of my now empty scrotum through the ring. My cock was poking straight out, and my balls were sitting above the ring on either side of my shaft. The pressure against my trapped nuts made it feel even better. John quickly buckled the thin leather straps to the pair of strategically placed buckles on the front of wide waist strap. There I was, dressed as a slut, a massive butt-plug harnessed inside me, John took several photos.
:”OMG! Daddy you are full of surprises what next?”
:”Get on your knees Sissy, it’s time to suck your Daddy’s cock.”
John sank onto the plush chair, waiting. Finally, I was going to see the object of my desire, a real live cock. His words spurred me into action, dutifully dropping to my knees before him. John stood above me; my eyes fixed on the growing bulge only inches from my face.
:”Good girl, you have shown promise my sissy slut. Let’s see how you go sucking cock.”
Lifting his butt from the cushion he hooked his fingers into the waistband of the white pouch; drawing them down over his hips slowly. Smiling down at me while revealing a smooth hairless shaft with an accompanying pair of smooth plumb sized balls hanging low in his hairless scrotum. His cock still only semi hard, was an impressive six or seven inches long. An involuntary moan escapes from my throat.
:”Mmmmmmm, Daddy, your smooth like me, like father like son.”
I give out a little girlish giggle as I reached for his cock. The weight of it was the biggest surprise, lifting John’s cock up, I planted several kisses on the fat bulbous head. My free hand cradled his large balls, rolling them in my palm like a pair of Chinese worry balls. But these balls do not chime when the smack together in your hand.
:”Blow Daddy, Sissy Boy, suck your father’s dick you fucking crossdressing whore.
Opening my mouth taking just the large head inside, sealing my painted lips around his shaft, I started sucking while my tongue was busy circling his urethra. My actions had immediate results, his dick grew larger in my hand, swelling so that my fingers only just met around his girth. The reward for me, was a flood of precum, lapping it up like a kitten with a bowl of milk, brought another loud involuntary groan from me.
: “Mmmmmmmmmmmmmm.”
John’s cock now stiff as a board, a good eight and a half inches of prime male cock meat, the veins standing out. I felt my mouth watering in anticipation, moving a little closer, scooting between his knees. Looking him directly in the eye I slowly licked my way along one side of his shaft down towards his big nuts. Kissing, licking, and sucking on each of them in turn, my fist wrapped around him pumping as I licked my way up the other side. Opening wide I engulfed his fuckstick, feeling it as it bumps against the back of my throat. Controlling my gag reflex I push further, taking his entire shaft into my gullet, my nose was hard against his pubic bone, his heavy balls cradling my chin. Stopping still for a few seconds, my eyes still holding his. A moan comes from me, vibrating around his cock as his hands come up to grip and guide me on exactly what he wants.
: “Aghhhh, that’s the girl suck Daddy’s, cock you fucking cross-dressed whore.”
I am happy to comply, siding back for a breath, my cheeks puff in and out as I gasp for a breath. His hands holding my head tighten, telling me it was time his flagpole cock was back in my throat. Sliding down his lengthy cock, revelling in the way his dick bumped its way deeper, my eyes began to water and on my next breath I coughed a gagged a bit. It did not stop me from going down on him repeatedly, his big fuckstick invaded my gullet, my throat was full of cock, I was in paradise. Loud obscene gluk, gluk noises filled the small room, while I was trying my best to make John cum.
: “Yeah, that is it my little whore, suck your Daddy’s hard cock, you are nothing but my cock sucking cross-dressed little slut. But that is enough for now cockslut, it is time Daddy fucked his slut of a daughter, get on the bed, show Daddy how good you are.”
Pulling back John’s thick tool slipped out of my wet sucking mouth with a pop. Clambering onto the bed, my plugged ass facing him, I looked over my shoulder as he approached. Feeling his hands massaging my ample buns made me moan like a perverted whore that I am.
: “Do not be in such a rush, my pretty cross-dressed whore. Daddy’s gonna take his time.”
He started to kiss my butt cheeks whilst tapping the huge, harnessed butt-plug, sending waves of delight coursing through my body. After a few more photos from behind showing my positioning, the harnessed plug, my ringed cock pointing straight down leaking precum like a dripping tap. John started to unbuckle the leather straps, leaving in place the chrome ring trapping my balls deep inside my body.
: “Mmmmm, okay Susie, let us see you get that tiny plug out my sweet cockslut. It is time for your reward for sucking your Daddy’s cock.”
Reaching back, gripping the wide base I tried to pull it out. My poor asshole was not going to give up its invader easily. I had to pull it back several times until my sphincter relaxed a little. I could not help myself I was moaning and groaning like the cockslut I truly am. Eventually I won the battle, my gripping shitter relaxed enough so that the plug finally slipped free. John took it from me, my asshole gaped open, I was lucky that it was not prolapsed. Joining me on the bed John, positioned himself behind me. John’s large cock nestled between my butt cheeks, I felt his heavy balls sliding over my wrecked sphincter as he started to dry hump the crevasse between my buttocks.
: “Please Daddy put your fuck-stick inside your slutty fucktoy, she needs to feel you inside her. Fuck me, Daddy. Fuck me hard and fast.”
Feeling the mattress moving under his shifting weight, I readied myself for the moment I had dreamed of since our first phone call. The head of his cock slid inside easily, I pushed back against him, taking another inch, showing how eager I was for him to fuck my asshole.
: “Susie your asshole feels like a real cunt, only thing different is you are not wet and slippery like a real one. Daddy has the solution though.”
I felt empty when he pulled his cock out, the shock of the cold lube as he squeezed it both outside and a large dollop straight into my gapping anus, brought a groan of unadulterated pleasure from my throat. His hands gripped my hips, fingers pressing into my skin, he drove his cock into me in a single powerful thrust. John’s hips smashed into my buns repeatedly as he thrust forward and pulled my body backwards onto his pounding rock hard monstrous cock. His heavy balls slapping against my floppy, empty nut sack on every stroke.
: “Fuck Daddy, your cock feels amazing, you’re filling me, fuck me, fuck me, fuck me, fuck me.”
His big dick flashed back and forth driving deep into my slutty boy cunt, my rock-hard dick swaying with the force of John’s fucking, pre-cum leaking from the tip, dripping onto the bed. Every time John hit bottom my trapped balls were being squashed inside of my body, sending waves of pleasure coursing through my mind. As my orgasm approached the pressure of my trapped balls grew, and when my little cockett exploded, spraying sticky white jizz all over the bedspread, my nuts felt like they were in a vice. The pain was delirious, sending me over the edge, I whimpered as my semen coated at patch around two inches in diameter. In my orgasmic stupor I screamed.
:”Oh God yes Daddy fuck my asshole, faster Daddy, as fast as you can. Piledrive that magnificent dick into your slutty fucktoy.”
John slapped my upturned buns with wild abandonment, while continuing to pound away at my slippery stretched fuck-hole. Suddenly he pulled out, sliding his cock along my ass crack, his big balls sliding across my wrecked sphincter brought fresh moans from my throat. John’ cock spewed his cum over my back, my buns and the last of his orgasm was deposited in my willing rosebud.
Pulling out John ordered me to clean his dick.
:”Clean Daddy’s tool you fucking whore.”
In a flash I spun around and gobbled his semi hard fuckstick, relishing in the taste, a mixture of cum and asshole. I was in heaven, not only had I just taken a cock in my shitter but now I was cleaning that cock with my mouth. Just like a dirty fuckpig would do for their master. Once I had finished cleaning John off, he undid the harness, wiped his seed from my ass and back, then he told me to get dressed. He dropped me back at my vehicle, smiled saying.
:”Next time Susie I think you can come to my office and suck Daddy’s cock.”
Of course, I agreed, but sadly he never called to arrange a time and date. I never heard from him ever again, he only liked fucking me the once. I do not know what happened to the photos he took, somewhere out there are the pictures of my dressed up, a massive butt-plug in my slutty hole. I have searched all over the web but sadly I have never seen any of them. John if you read this PLEASE, PLEASE, PLEASE contact me, my phone number is still the same.
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