Adult Sissy Stories & More


IT ALL BEGAN EASILY ENOUGH by Sissy Erica (Part 2)

“You know, I’ll expect you to return this favor for me.”

“Ye, yessir,” was all my trembling mouth could manage in response.

“Good girl, Alicia.  You like this, don’t you?”

“Yes, sir,” I managed to state a little more emphatically.


“Excellent,” he smiled up at me, “I’ll expect you will learn to like doing to me what I’m doing for you right now.  I’ll expect you to do it a lot, too.”


Before I could answer he was sucking on my cock again and after another couple of minutes I was shooting forth my white hot cum into his suctioning mouth.  My whole body trembled from the sensations and I was loving it!


Again he stood and kissed me and this time I did not resist at all.  When he put my arms around him, like a girl would, I understood and complied.  We necked for a few minutes, standing there, when he finally broke away and told me, “You are a wonderful kisser for a boy or a girl.  You will do well.  We need to stop or I’m going to get too carried away and we’ll never have lunch.”


I suddenly realized I was more interested in what we might do than have a bite to eat.



“Well, lunch first and then we’ll have some fun this afternoon with you dressed pretty in a nice dress and high heels and make up.”


He helped me step into my panties and then clad as I was led me downstairs for lunch.


At first it seemed odd to be wandering around his house clad in just bra with breast inserts, panties, garter belt and nylon stockings, and a pair of women’s flats on my feet.  The more I stayed dressed that way the more natural it seemed and I luxuriated in what I was wearing.


Subconsciously, I knew I was turning Mr. Ferguson on and found that a strong appeal for me.


He had me sit at the table as he fixed us a tuna salad and commented that for dinner he would be teaching me some rudiments of cooking which every girl needed to know.


“Maybe I’ll even have you try your hand at barbequing our steaks for dinner,” he told me as he sat down at the table.  “You’ll be pretty well hidden from view at the barbeque out back, as you know, and it shouldn’t be a problem for you to be out there in a dress, make up, and high heels.  Think you would like that?” he asked in conclusion.


“I’d love it, Mr. Ferguson,” I answered and started in on the salad he had set before me.


“I’m starting to think you won’t want to go back to being a boy by the time this weekend is over,” he laughed.  “You’re having too much fun being a girl.”


“I just had no idea, Mr. Ferguson, and when you proposed my learning about how girls look at things I never considered trying being a girl to learn.  I guess if girls do it with each other as a way of training for dealing with us guys then I’m glad you are being so kind to me.”


“Well, this sure is a good way for you to learn and sort of feel like you are on the inside with girls when it comes to their perspectives.  You’ve a lot to learn but this weekend will be good for you and a lot of fun, too.


“I hope this is fun for you, Alicia,” he concluded.


“Oh, Mr. Ferguson,” I gushed, blushing a little, “It is incredible.  I can hardly wait for our further adventures.  You are very kind to me and play a wonderful boyfriend, too.”


“Well, just think of me as your boyfriend for the rest of the weekend and you’ll love it.”





After lunch he took me back upstairs and continued my transformation.  I already thought I looked like a girl but would be amazed at the transformation that was about to take place.


Standing me next to his bed, he dropped a silky pink nylon full slip over my head and helped me get my arms through the shoulder straps.  A few quick adjustments to the slides on the straps and I found the slip draping perfectly over my breasts and hips.  Glancing at the mirror I found a girl staring back at me and realized I was her!  It felt wonderful, enjoying the undies I already wore, and it made me realize how lucky girls were with what they could wear.


Seating me at his wife’s make-up table, he set to work on applying all the items to my face that a girl would.  He explained the use and need of each, starting with a foundation base and then finishing it with my lipstick as the last step.


“The real trick, when assuming the ‘persona’ of a girl, is not to use too much make-up.  Understatement works best and that is just what girls do.  Too much and you look both slutty and false.  You don’t want to look ‘false’,”  he advised, “As that is a tip off you aren’t a girl.”


My lips seemed fuller with the new color and gloss while the lip liner made them look larger.  My eyes were more open and innocent looking with his soft touch of eye shadow and false eyelashes without much mascara.  A bit of rouge on my cheeks made my cheek bones a bit more prominent.  I was so convincing as a girl with a boy’s haircut.


“What about my hair?” I asked.


“Everything in its own good time,” he replied and clipped a gold dangly hoop earring on each earlobe.  “You’ll get used to the pinching and if you want them pierced we’ll have to talk about that as your parents will likely object.”


Next came a blonde wig that had soft curls cascading down over my shoulders.  Now I really did look convincingly like a girl.  I was both proud and pleased with my transformation and the events of today made me glad I’d agreed to do this.


“I just love this, Mr. Ferguson, and am so surprised at myself.  You must have spent a lot of money on the false breasts and other items.”


“Not that much, dear,” he pointed out, “I do have friends still in the business I was in and they gave me some terrific discounts.




 “Now, let’s get a dress and a pair of high heels on you so you can finally look like the young girl you want to be.”


“When I took your measurements, yesterday, I was also checking both shoe size and dress sizes.  Luckily, almost all of my wife’s things will fit you perfectly.  This dress is new but high heels were hers.  Let’s see how it all turns out.”


The dress was a silk shantung affair of oriental manufacture.  It nipped in at the waist and fit my new bosom perfectly.  The skirt was straight, almost restrictive in its tightness, and the hips seemed just a bit too large.


Mr. Ferguson stood back and looked me over, assessing my new female appearance.


“Yes, you’ll eventually need some hip pads inserted into your panties.  However, we can do that later when we’re ready.  Now, let’s see how you get on walking about in high heels.”


With that he had me sit on the velvet bench at the foot of the bed and he slipped a white high heeled pump on each foot.  The spike heels measure four inches and looked pretty intimidating to me to walk in.


“Okay, time to learn to walk like a girl,” he said and kissed me on the forehead as he helped me stand.


“Oh, my,” I muttered as I stared at myself in the mirror.  It was as if I was now replaced by someone else and she was a very pretty girl in her late teens.


Walking was entirely something else.  I nearly fell after only two or three steps.  He held my arm and guided me around the bedroom cautioning me to take shorter steps, place one foot almost directly in front of the other, and lift my legs at the knees not throwing my foot out in front of myself like a guy does.


“You’re going to continue to need practice, but by the end of the weekend I think you’ll be walking around in high heels as good as any girl your age,”  he told me.


With that he led me to the stairs and told me how a woman navigates steps.  With him leading the way I carefully stepped in a somewhat diagonal manner down the stairs and was real proud of myself for getting to the first floor without tripping.


“Congratulations!” he boomed and hugged and kissed me.  Then he kissed me again and I found his tongue invading my mouth once more.  I remembered he said his role was to be the



“boyfriend” so I could learn and soon we were standing there necking and I found my cock beginning to grow inside my panties again. 


What was further surprising was my noticing he had also grown a hard-on and I wondered how big he was, was he cut or uncut, and that I liked knowing I was turning him on, too.    “Just like a girl,” I silently thought to myself.


“You really make an attractive young lady, Alicia,” he murmured into my ear as he kissed me there and taunted me with his tongue sliding inside my ear.  “You are turning this old man on like mad.”


“I’m glad, Mr. Ferguson,” I whispered back between kisses.


His hand had slid up to the front of my dress and was massaging my silicone titty and just the idea of him doing that was also stimulating for me.


With his other hand he guided one of mine down to the front of his pants and I found him sporting a hard-on.  I knew I was the cause and could not resist squeezing it and feeling him through his slacks.


“Take it out, Darling,” he whispered between kisses, and I dutifully unzipped his pants and found he was not wearing undershorts. 


His cock sprang free and I was then told to undo his belt and drop his pants for him.  I held his cock with my other hand, amazed at how eager I was to stroke him, as I undid his belt somehow and his slacks hit the floor.


“I want you to do more than just stroke me, Darling,” he intoned as his hand on my shoulder began to push me downward.  

I knew what was expected and was actually eager to try sucking on a man’s cock.  Twenty four hours ago I’d have never believed I’d be doing this much less wanting it.


My silken clad knees slipped slightly on the soft plush cut carpet, due to the slipperyness of my nylons, and I stared at his almost 8 inch cock.  It was larger than mine and uncut.  It was the most intriguing thing I had ever seen and I began to realize I was beginning to react more and more like a girl!


I kissed the head of his cock and then slipped my lips around it as I gently massaged his balls with one hand and held on to his leg with the other.  I imitated what he’d done to me.  Soon my eager slurping sounds were filling the room and I knew he was happy with me.


Looking up into his eyes I noted he was being thrilled by how I was sucking on his man meat and knew I wanted to do it the best I could.  My tongue rasped along the underside of his cock head, every so often, and each time he jerked a bit in pleasure from it.


Suddenly, he held my head and began thrusting into my mouth.  I wasn’t able to take him down my throat but suckled as hard as I could and soon he was filling my mouth with his cum!


I kept on slurping away until he could give me no more and then finally let his cock slip from my lips.  I was somehow reluctant to let it go.  I swallowed all of his cum and relished in the subtle taste of it and knew I would want more whenever I could.


Pulling me up he kissed me deeply and murmured, “You swallowed all of it, didn’t you.”


“Yes,” I answered shyly, amazed at myself for so enjoying what I’d just done with a man.


“I’ll want you to do this again, and I hope you will,” he whispered softly into my ear.


“I think I’m already addicted to it,” I whispered back and we both giggled as we stood there and necked in his living room.


Taking my hand he led me out onto the screened porch which was shielded from view of any passersby.  Seating me on the cushioned glider he went inside to get us each an ice tea and told me we needed to discuss some things.


I sat there reveling in how it felt to wear all the wonderful garments that kept caressing my body and how I loved taking the role of a young girl.  A very horny one, at that!


Returning moments later, he handed me an iced tea and sat next to me holding my hand.  I was loving this.


“I hope I am not taking you too far too soon,” he said softly as we clinked out glasses in a toast to what I’d just done to him.


“Not at all, Mr. Ferguson, I’m loving this and never knew I would want to do any of this stuff, including dressing up in girl’s clothes.”


“Do you want to stop, right now, or do you want to go on to the next plateau?” he asked.


“Oh, please, all the plateaus you can think of!  I want to try them all!!  This is so thrilling for me and I am beginning to understand how girls think.  I know there is a lot I need to still learn, but I’m loving this so much!”


“Then I’ll be wanting you to surrender your body to me completely,” he told me.  “This will mean more fun and delight for you, but you need to be ready for it.”


“I thought I’d already surrendered my body to you, Mr. Ferguson,” I giggled, “When I sucked you off a few minutes ago.  Besides, I admit I want to do that again for you.”


“I meant beyond that, Honey,” he informed me.  “To help you affect a more girlish gait I am going to take you upstairs and give you an enema.  Once we’ve that out of the way I’m going to insert a plug up your bottom that will somewhat force you to walk with a hip swivel like girls seem to know how to do instinctively.”


“Excuse me, an enema? Isn’t that a bit extreme, and what’s a plug?” I wanted to know.


“Not really,” he said softly as he put an arm around my shoulders and held me close to him.  I was loving this sensation of being treated like a girl, again, and snuggled in without protest.

“You need to open your body up to me so I can help you achieve what you need.  You may well find out the enema is extremely sensual, for you, and wearing a butt plug will stimulate you further and, I’m afraid, make you very very horny.”


“I already am!” I exclaimed in return, giggling like the schoolgirl I felt I’d become.


“That’s great, because tonight I’m going to want you to wear a long silky sheer nightgown over your bra, garter belt, and nylons when you go to bed.”


 “Wow,” I thought, he is going to really keep me as a girl all weekend.


I found myself asking, “What color is the nightgown I’m to wear tonight?”


Already I was succumbing fully to his plan.


“A soft feminine pink,” he responded, “Which will help you achieve the frame of mind you need. I think you will love sleeping in nightgowns,” he concluded and I instantly realized he would expect me to wear a nightgown each night.


My dress front was already showing my reaction to his commentary because my dick had gotten hard again.


“Looks like you are eager to start your next plateau,” he laughed and stroked my cock through my dress, slip, and panties.  “However,” he added, “We need to give you a rest from all this sexy activity.  I’ve some teenage girls’ magazines you need to study as you relax.”


Mr. Ferguson handed me several magazines like, “Seventeen”, “Glamour”, “Woman’s World”, etc. and told me to take my time reading them and if I felt like a nap it would be just fine.


“I’ve some paperwork to do and friends to call for social things,” he told me, “So you just relax and enjoy being a girl here on the screened in porch.  Stretch out on the glider and snooze a bit, too, if you want.”


The magazines were more interesting than I had thought and soon I was fascinated with the ads for lovely clothes and some of the stories of romance and articles about dating.  It was a surprise to find a few articles that were quite candid in what to do about a boy who’s hands keep trying to wander to a girl’s breasts or up under her skirt.  All this made me realize girls were concentrating a lot more on relationships and sex than we boys had been giving them credit for.


Before long I had drifted off to sleep and was soon dreaming I was a young girl out shopping dressed nicely in a pretty outfit and high heels as I wandered from store to store choosing some very intimate items without anyone questioning me.


A gentle hand on my shoulder wakened me and Mr. Ferguson told me I’d slept a good share of the afternoon and it was nearly 5 o’clock.


It startled me to wake up and not know where I was and find myself wearing nylons, high heels, and be fully dressed as a girl.  It took me a moment to come to my senses and recall what all had happened to me this day.


“Oh, sorry, Mr. Ferguson, I really fell asleep.”


“Yes, you did, Dear, and we need to get some things done around here.  Five o’clock is cocktail time in this house and I’m going to permit you to have a glass of wine.  However, we need to do some other things for you first.”


“Oh, okay, but first I really need to go potty,” I said amazed at myself for even commenting like a girl would instead of saying, “I need to take a piss.”


“Come on,” he offered as he took my hand and pulled me off the glider, “Let me help you up.”


Sliding off the cushions my dress and slip hems rode up my legs well past the top of my nylons.

“You’ll need to be a bit more careful in the future if anyone else is around,” he grinned at me, “That is really sexy flirting.”


“I’m sorry,” I mumbled and began to blush.


“Don’t be with me,” he commented, “I love it!  You really have lovely legs.”


I felt flattered and loved hearing that from Mr. Ferguson.  He led me through the house and to the stairs.


“We need to see how you navigate going up stairs compared to down them,” he told me, “You are still walking a bit like a boy in high heels but I think we can cure that shortly.”


I managed to get upstairs all the while knowing he was watching my backside and looking up my dress at my legs.  It was a bit exciting for me.


In the bathroom I was about to close the door but he stayed with me.


“No, no,” he admonished me, “I need to be your ‘shadow’ all the time to make sure you obtain the habits of a young lady if you are going to have that inside track on how they think.”


As I stood before the toilet ready to hike up my skirt and lower my panties he was again correcting me.


“No, Alicia, not that way.  Boys stand to piss, girls drop their panties to their ankles and sit on the toilet to pee properly.  You must always do it that way, too.”


It was a bit embarrassing to turn and lower my silky panties down over my nylons, the sensation once again making me shiver in pleasure, and then sit there and aim my pee inside the toilet bowl.


When I had finished Mr. Ferguson had me softly tap my penis dry with toilet paper, like girls do to their pussies, before I could get up.


I was about to pull up my panties when he advised me to take them off as we needed to get another task completed.  As he did so he was filling an enema bag with warm water at the sink.


“Get down on all fours on the large towel on the floor,” he directed me.  I then felt him lifting my skirt and slip up over my ass and draping them well up my midsection out of the way.

He greased up the nozzle, as I watched, and then moved behind me and told me to just relax and let the end of the nozzle slide inside my anus.



Easier said than done, I quickly realized, but with gentle persistence on his part he made me relax and the nozzle end slowly entered my nether channel.

Gradually, he eased the slippery hard plastic into me and then released the flow of water from the bag which he had hung on a hook behind the bathroom door.


“ohhh,” I moaned gently as the water gushed down the tube and into me.  As that was happening he kept slowly easing the nozzle in and out of my anus but never taking it all the way out.


Despite myself I began to slowly rock back and forth to meet the gentle thrusts he was giving me.

“I can see this is becoming enjoyable for you, Alicia,” he whispered in my ear as  he reached around me and stroked my now stiff cock.  “Maybe you and I will want to do this often.”


Soon I was feeling quite bloated with water and he eased me up to a standing position.  Guiding me back to the toilet he had me sit on it but scrunch forward so he could deftly remove the nozzle from me.

Instantly the water shot out of me into the bowl and I felt instant relief.  I was glad this was over, even though it was a bit of a turn on, since it was a bit humiliating.

Before I could get up, though, he had refilled the bag and bade me to wipe myself clean and then get back on all fours for him.

This time he had a different nozzle on the end of the enema tube and it was shaped like a cock.


“This will make it easier for you to accept the butt plug,” he advised as he liberally greased up the false phallus.  “It won’t hurt you and will probably feel a bit nicer than the nozzle did.”

With that he got behind me again and put the head of the false cock up against my anal opening.  It took a bit of trying, on my part, to relax but finally he had managed to ease the head of the enema dildo inside me.


“ohhhhh,” was all I could muster as he slowly worked in further and further inside me.  Soon he had all six inches buried inside my ass and I was becoming accustomed to having it there.  Then he released the water and I felt my rectum taking on another bag full.

As before, he began working it in and out of me as the flow entered me.  I couldn’t resist rocking back and forth to meet the thrusts and he began stroking my cock again.


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