Adult Sissy Stories & More


IT ALL BEGAN EASILY ENOUGH by Sissy Erica (Part 3)


“You’re enjoying this, aren’t you, Darling,” he commented as he worked on me driving me to a fever pitch.


Soon I as filled with the other bag of enema water and also wanting to cum.  However, he held me close and led me back to the toilet so I could void the contents of the enema. 


After wiping myself clean and dry he had get back on all fours once more.  I began to wonder how many times he would be giving me an enema.

He produce a metal ring with an inside diameter of nearly two inches.  From somewhere he had ice cubes in his hand and quickly my hard-on disappeared and even my balls seemed to shrink.


“Good girl,” he intoned and then quickly slipped the ring up my cock to the base and managed to get both of my balls through it, too, before I started to swell up again from his fondling.  Now I had a metal ring surrounding my sensitive area and it would prevent me from losing my hard-on.


“Perfect, Honey,” he said softly, and then he fitted a leather strap around my waist.  I was now quite curious about what he was going to do to me but knew better than interrupt him.

The leather waist strap had another at the very front that he pulled down and looped it through the metal ring and then closed the snaps on it.


From the back of the waist band was a second strap that was longer and could be pulled between my legs to the metal ring around the base of my cock and balls.

From the counter he brought over a pink cone shaped device.  It had a bit of a rounded top and flared out to a couple of inches across and then nipped in to about a half inch in diameter below it and had a flat rectangular base.

Liberally greasing up the cone I realized this was the butt plug he was referring to earlier.


“Now, just relax and let it enter you,” he said softly as he began probing my anus.  It took a few moments and then the rounded tip entered me but would not go further.  It was larger in diameter than the dildo and I wasn’t sure it would fit.


“Just relax, it’ll work, Dear,” he whispered, “And will soon feel wonderful for you.  This is the toy that will help you learn to walk exactly like a girl.”


It took another minute or two and it was finally snugly in my ass.  Surprisingly, it felt very nice.  

He then held out a small piece of leather that he fitted around the base of the butt plug and it had two sides that hung down about an inch each with snaps on them.  These he fitted around the strap that went between my ass cheeks and snapped them closed.


Now he had the butt plug in place in me and it would not come out until the snaps were released.  At the same time the cock ring was keeping me hard and my arousal was a great surprise to me.

This day had been one of nothing but shocking surprises and I began to wonder how many more were in store for me as I moved to each plateau.


“Okay, Honey,” he told me, “You can stand now and put your panties back on.”


I did as he told me and was a bit stunned to feel the butt plug moving inside me as I moved my legs to step into the panties.  The look on my face gave away the sensations I was now experiencing.


“Almost feels like someone is gently fucking you, doesn’t it, Alicia?”


“Ye, yes sir, I guess that’s what if feels like,” came my surprised reply.


“You’ll like it and at the same time it will force you to walk like a girl.”


He held my hand as I walked through the master bedroom, down the hallway, and traversed the stairs to the living room.  My quiet sighs and slight moans reinforced what he wanted of me.  I was astonished to feel this plug bobbing up and down inside me with each movement and wanted to walk more and more to keep it doing it.


“You’re already walking more like a girl,” he mused and then poured me a glass of red wine.


Taking my hand in his, as we walked back to the screened in porch, I felt like a girl who was slowly getting well fucked and loving it.  I was transitioning into young womanhood.


“Here’s a toast to you, Alicia, on becoming a young girl and tonight you will experience fully what it is like to be a woman.”


With that we clinked our glasses, sipped a sip, and then he kissed me as his free hand managed to push the butt plug further into me and then ease it out.  My moans were music to him and my knees visibly trembled inside my nylon stockings.  I didn’t think to question his comments about my experiencing fully what it would be like to be a woman.


Taking my hand he led me to the glider and he had me ease down softly onto the stuffed cushions.


“You don’t ever want to sit down hard while wearing a butt plug, Darling,” he told me, “It can really hurt.”


I assumed he was right as just sitting down seemed to ease the plug further up my back channel and I squirmed a bit at the feeling of it.  That didn’t go without notice by Mr. Ferguson.


We chatted awhile and he inquired what I thought of the young girl’s magazines he’d given me to read.  He seemed pleased to learn I found them interesting and there were several articles I really thought might be fun to complete reading.

We held hands on the glider and sipped our wine as we chatted.  Pretty grown up for me, but at 18 you can have certain drinks in our province.  I felt like a young woman on a date and I was really loving it. 


“Girls are sooo fortunate,” I thought to myself as we sat there.


Eventually, Mr. Ferguson told me it would soon be dark and we needed to have our dinner.  He was going to scurry into the kitchen and fix a salad and then we could team up on barbequing the steaks he had gotten to celebrate my transformation into a young woman.

A short while later he came back and asked me if I’d like to help with the barbequing of the steaks!   I’d hardly nodded my head when away we went through the kitchen to grab the steaks.


He fired up the grill and showed me how to grease up the grill top so the meat would not stick.

“You need to always use something to grease up where you are going to put your meat,” he grinned.

“Unless my mouth is wet and waiting for it,” I grinned back and we smooched as we stood next to the barbeque.  Before long he was thrusting the butt plug into my ass again and it was turning me on like crazy.


“I think we need to stop,” I whispered in his ear, “Even though I don’t want to.  However, if  you keep that up I’m going to cum in my panties.”

We managed to control ourselves and finish cooking the steaks and then he took me back to the porch where he had somehow set the table and he then lighted a couple of candles.  It made for a very romantic setting for our dinner.


We enjoyed our meal and he told me dessert would be special tonight.  I was curious and hoped I was the dessert.

He poured us each some more wine, although I didn’t need any as I could already feel the effect of my first glass.  We sat there and sipped our drinks and chatted about a variety of things until he turned the conversation about my wearing only girl’s lingerie, a dress, stockings, high heels, and makeup along with a wig.


I admitted I was loving it and his gift of the panties, the other day, had started the whole thing.


“I had hoped it would, Alicia,” he said softly.  “I’ve been wanting you for a long time and this is a great way to make you happy, you can learn what you need to find out about femininity, and maybe more.”


“I suspect you plan for more in the plateaus you referred to,” I commented over the rim of my glass as I smiled at him.


“Tomorrow you will be learning a girl’s domestic duties.  I want you to learn some basics about cooking, which your mother will love, as well as house cleaning, etc.  You will wear a  maid’s uniform and I’ve another pair of high heels that will fit you to go with the uniform.”


“Wow,” I enthused, “That sounds like fun.  I’m really enjoying living like a girl.”


“Great,” he said as he looked at me from across the table.  “Tonight you will learn even more.”

As he said this I suddenly felt a slight buzzing in my bottom and it seemed the butt plug was vibrating.


I must have gotten a funny look on my face as Mr. Ferguson just looked at me and smiled more broadly.


“Does your butt plug feel nice, Honey?” he asked and suddenly the vibrations increased quite a bit. 

It was all I could do to sit still in my chair without wiggling all over it caused by the butt plug.


“Wha, what are you doing?” I wanted to know and the vibrations got even more pronounced.


“It is a remote control that is tuned in to your butt plug, Darling,” he smiled.  “I think it must be feeling very good to you.  Now let’s try this,” and so saying the butt plug not only vibrated but began to pump up and down inside my ass!!


“That’s it, Alicia, just let it take over and give you a nice ass fucking.  I’m sure you are loving it from the look of ecstasy on your face.”


I was now holding onto the edge of the table as the butt plug took on a life of its own.  It was vibrating strongly, so strongly one could hear it, and it was thrusting up and down inside me.


“Oh, o, oh, um, M, Mr. Fer, Fergus-son, I, I’m go-going to c-cum!”   With that I began flooding my pretty pink panties with my gism as the tool worked away on me training me to accept being fucked back there.


It took me a few minutes to settle down and he didn’t reduce the vibrations or thrusting until he knew I was done cumming.


“Let’s take you upstairs to the bathroom and get you cleaned up and into a fresh pair of panties,” he told me.


Upstairs he gently washed me with a warm washcloth and then gently dried me and powdered my cock and balls before helping me step inside a fresh pair of sheer pink panties and snug them up in place.  .


I was still a bit weak from what I’d just been through and also wondered if the wine was having an effect upon me, too.


“Come on down to the family room,” he told me, “And we’ll watch some TV after I clean up our dishes.”


I went downstairs with him but insisted on helping clean up after our meal.  The butt plug was now silent in my ass but I was constantly aware of it and my cockette was beginning to show some signs of life.  I was surprised at how all this kept getting me hard so quickly!


With the remnants of our repast put away, and all the dishes and other items washed and drying, he took me into the family room and had me sit on the sofa facing the large screened TV set.


“I’ve a couple of movies that you might enjoy seeing,” he said and clicked on the remote.  As soon as a picture came up on the screen he clicked another remote and the video player began.


It showed a guy and a gal necking in her living room.  He was trying his best to get his hands up her skirt past the tops of her nylons.  However, she pretty successfully fended him off and allowed him to open her blouse and eventually unhook her bra.  Soon they were kissing and he



was feeling up her breasts and then suckling on them.    I found it stimulating to watch as I’d never seen a movie like this but had heard of X rated movies.


Mr. Ferguson was now sitting next to me with an arm around my shoulders as we watched the video.  He was holding me close and I was loving the feelings of being cuddled by a man.


“Here comes the better part,” he whispered in my ear and then kissed me.  “Watch what happens.”


The couples necking had become more heated and she had unzipped his pants and was slowly jacking him off as he suckled on her breasts.  He was still trying to get his hand up under her skirt and she was twisting to and fro trying to fend him off.


Finally, he managed to get his hand into her panties and began feeling her up more but, all of a sudden, he stopped and looked at the precious platinum blonde with total surprise on his face.


“What’s this?!” he wanted to know and pulled her skirt and half slip all the way up to her waist.  Revealed to the camera was more than just the tops of her nylons, garter belt, and sheer white panties, but she had a cock, too!


“I’ve been afraid to tell you,” she muttered and began to blush.  “I want you as my boyfriend but how could I tell you I am a boy, too?”


“It, it’s beautiful,” he whispered and pulled her cock out of the leg opening of her panties.  “I think it is great you have a cock, Darling!”


Her head fell back and her eyelids fluttered as he lowered his mouth to her cock and began sucking her off.


It wasn’t long before he had her panties off, had shucked his jeans and shorts, and was fucking her with long hard strokes as she wrapped her arms and nylon clad legs around him and urged him on.


By this time I was fondling Mr. Ferguson’s cock, which I had freed from his trousers, and his hand was up under my skirt feeling me through my panties.


“You are hard again, Sweetie,” he murmured to me between kisses.


“So are you, Darling.  I need to do something for you, and lowered my head to his cock.


However, he had other plans. 



“No, no, Honey, let’s go upstairs to the bedroom.  We can watch more of this movie, and others if you want, later.  Right now I want you.”


I offered no resistance as he led me upstairs and fondled my ass on the way up.  In the bedroom he helped me out of my dress and slip before bringing me a floor length sheer chiffon nightgown in a delicate pink.


Soon I was standing before him in the soft light of his room wearing a beautiful nightgown, my bra and inserts, panties, garter belt, nylons, and high heels.  I had already forgotten about the butt plug and was eager to get my hands on his cock!


He quickly stripped nude and then embraced me.  Quickly we were necking and stroking each other and I was about ready to erupt.  He could sense it and suddenly stopped and told me we needed to take the butt plug out as it was time.


He undid the harness from around my waist and unclipped the wrap holding the butt plug.   His easing it out of my ass suddenly had me feeling like I was really missing part of me.  Then the rest of the harness was removed from me along with my dear pretty panties.


The metal cock ring he left in place and I didn’t ask.


Taking me to the bed he had me lay down on my back with my head on the pillows.  Then from his nightstand he produced some lubricant called “Anal Ease” and quickly slathered it all over his cock.  Now I realized what he meant when he said I would soon experience fully what it was like to be a woman.


I kicked off my high heels, when he lifted my legs apart and I felt him nudge my anus with the head of his cock.  By this time I wanted what I knew was coming.  I wanted to be just like the he/she in the movie we’d just been watching.


“Oh, ohhhh, Mr. Fer-ferguson, You, ohh, are soo b big,” I muttered as he slowly worked he head of his cock in my ass.


“I hope it isn’t hurting, Honey,” he whispered, while kissing and licking my ear, as he kept easing more and more of his dick into me.


“No, no, it’s a bit, uncomfort….. ohh, no, I kind of, li-like it,” I moaned as he slowly but surely pushed his cock further into me.  The butt plug had prepared me well for this.




Then he slowly withdrew it most of the way and then thrust it back in.  Soon he was thrusting in and out of me rapidly and all I could do was wrap my arms and legs around him and try to work with him.  It seemed I was constantly moaning and wanting more.


“Ohhhh, fuck me, fuck me, make me your girl in all ways!” I screamed out not caring if the neighbors could hear us or not.


“I knew you would like this,” he whispered in my ear as he was tonguing it turning me on even more.  Then he gave me a deep French kiss and I felt my cock rubbing between our tummies as he kept on rapidly fucking me.


“Ohhh, I, uh….” I stammered, “I, I’m g-going to to cum!” and suddenly felt myself wracked with the throes of shooting my cum onto our sliding tummies as he fervently fucked me.  Then, he suddenly shuddered and I knew he was flooding his cum inside me.


It was a strange thing, knowing I’d just made a man cum by letting him fuck me.  Even now, as I sit here typing this while wearing just a pair of sheer black trunk leg panties, I find recalling it exciting for me.


We lay there, in each other’s arms and he kissed me again and told me what a lovely young girl I had become.  I responded by letting him know I was loving every bit of it.


With that he took me into the bathroom and helped me out of my lingerie, some of it cum soaked, and then showed me how his wife would lightly wash and rinse her things out in the sink and hang them up to dry. 


That done he gave me another enema and, after I’d voided the water and remaining cum from my ass, we stepped into the shower and washed each other thoroughly.  Showering together seemed so romantic.


We each brushed our teeth and I knew it was sleep time for both of us as it was getting a bit late.  He gave me a long white sheer chiffon nightgown that came almost to my ankles and had me put my bra back on with the silicone breast inserts also in the cups.


“You need to know how a girl feels sleeping in a bed with a bosom.”

It made sense and I didn’t question it.  Then we both were under the covers and I was snuggled up tightly to him spoon fashion and soon drifted off to sleep with his arm over me.


It must have been about 2 AM when I felt his cock probing between my ass cheeks and I awoke.


“What is it?” I asked in all innocence.  Instead of answering me, however, he soon was nudging the head of his cock against my anal ring which was still fairly well lubricated from earlier.


 “Ohhh, yesss,” was all I could mutter as he eased  his cock inside me and began slowly fucking me while we were still laying there spoon fashion on the bed. 


Mr. Ferguson fucked me for about 10 minutes before he came in me once more.  I was happy to be that attractive to him that he wanted to fuck me again and urged him on in sweet tones as he worked away at me.  I could almost feel his cum shooting into me and was so happy to have brought him off that way.


Soon I fell asleep, as did he, with his cock still in me and it wasn’t until some time later that he slipped out of me during the night when we turned in our slumbers.


I awoke first and began nuzzling his chest and kissing and suckling his nipples while my hand encircled his cock and slowly stroked him.


“A great way to wake up,” he said, grinning down at me.


“What way could be better?” I joked back and he had a response to that.


“How about a nice blow job before we get out of bed?”


Quickly I was kneeling between his legs in my nightgown sucking his hard on eager to be rewarded with a nice load of his gism.


He came quickly as I only sucked his cock for about 5 minutes before he was shooting his load into my waiting mouth.  I swallowed it all and didn’t miss a drop.


Kissing me deeply, he helped me out of bed and found a pair of pink satin high heeled mules for me to wear as slippers.


“Come on,” he said, “Let’s go fix coffee and breakfast.


We puttered around the kitchen, me wearing the sheer gown, bra and false breasts, and my mules while he remained nude.  I couldn’t help sneaking glances at his equipment while he showed me how to make pancakes and fix coffee.


“You will need to learn kitchen skills, like a girl,” he advised as we worked together on preparing our breakfast, “I can already see you are turning into a slut type girl, though, by the way you keep sneaking glances at my cock.


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