Adult Sissy Stories & More


IT ALL BEGAN EASILY ENOUGH by Sissy Erica (Part 1)


It all started out easily enough.  Mr. and Mrs. Ferguson had been our neighbors for many years.  Their backyard abutted our backyard, a bit at the side of the end, so contact was frequent but not too much so.  They socialized with different friends, maybe because my parents were younger, but were certainly nice neighbors.


Mr. Ferguson had a much older Chrysler sedan that, as a boy, I salivated over and he knew it.  Sometimes, when he was washing his car, I’d sit by and watch and then eventually help out.  We became good friends, even though I was just 15 and he approaching 60.


Over time they hired me to mow their grass and do other odd jobs around their place.  Mr. Ferguson retired from owning a dress shop and I thought my jobs would end but they made no changes when he retired.  With few summer jobs around I was happy to have some income as I had one more year of high school and Mr. Ferguson always had work for me.


Then, I was just 18, Mrs. Ferguson died.  It was quite unexpected and he was most sad.

My parents thought it nice that I had a summer job working on their lawn, painting, stripping wallpaper, etc. They felt maybe my presence would make the adjustment easier for him.  The two years of retirement had given them a chance to travel and I looked after the place in their absence.  He was tall and handsome as she was tall and beautiful.


One day, when washing the upstairs windows inside and out, Mr. Ferguson was going through some of her clothing.  He had a big pile of her lingerie on the bed and was apparently preparing to give it all away.  It was still laying there when I came into their spare bedroom to wash the windows on the inside.  He excused himself to go downstairs and make us some lunch while I continued with the window washing.


It was intriguing to see all these mysteriously lovely clothes piled high on the bed.  I was so fascinated I could not resist looking through them and picked up a pair of silky sheer pink nylon panties and examined them, even holding them to my cheek and enjoying them on my skin.


“They’re lovely, aren’t they?” I heard a voice behind me and was startled and embarrassed to be caught fondling his wife’s underwear.


“I, I, uh,” I began to stammer when he cut me off.


“No problem, Irvin,” he said.  “We all admire what the ladies wear and at your age it is normal to want to examine them.  We’ll keep it our secret, okay?”


I can’t tell you how relieved I was at his reaction but, reluctantly, and quickly, put the panties back on the pile of lingerie on the bed.

“You can keep them,” he said, surprising me greatly, “I’ll just be getting rid of them, anyway.”


I really didn’t know what to say and must have stammered some kind of “no thank you” but he

picked them up and handed them to me.


“Our secret,” he commented.  “No one will know.  They’re yours.”


I stood there a bit transfixed and didn’t know what to say.  I must have had a stupid smile on my face which told him all he needed to know.  My kneading the panties, as I stood there, was further proof he knew I wanted to keep them.


“I’m almost done fixing us a couple of turkey sandwiches,” he said, making me glad to change the subject.  “I came up to see what you wanted on yours.”


I managed to mutter that I would like some mayonnaise.


He smiled at me and said, as he departed the room to finish making our lunch, “You can try them on here and wear them if you want.”


He was gone before I could reply.


I chickened out and put them in my pocket and went back to washing the windows while trying not to think about the exchange we’d just had.


At lunch he noticed the lace sticking out of my jeans pocket and smiled.  “If you take them home to try on there, I suggest you tuck them in your pocket a bit further.”


I was embarrassed again and quickly did as he suggested.


The rest of the day went by with my eventually forgetting about the pretty panties stuffed down inside my jeans pocket.


“Tomorrow at 9?” he inquired, in reference to my finishing washing the windows, and I nodded my agreement.


Arriving home my parents informed me of plans to go away Friday, Saturday, and return late on Sunday to visit relatives I really didn’t enjoy.  They knew I didn’t want to go, but could not leave me home alone at my age.  If I was older it would be different.  What a bummer!



Tomorrow was Thursday, so I’d have to ask Mr. Ferguson if I could finish caulking and washing his windows on Monday.  Maybe he could wait until then for me to store the storm windows I’d taken down and put up the screens.  Luckily the summer heat had not come on yet.


The next morning found me arriving right on time and before I could get into explaining my dilemma about going away he asked me how I like wearing the panties the night before.


“How, uh, how did you know?” I stuttered.


“Well, they’re pretty nice to wear from what I understand, and knowing your curiosity, it was obvious you’d try them on.  I’ll bet you slept in them last night, too.”


By now I was blushing bright red and numbly nodded my head in admittance.


“Do you have them on now?” he asked.


Again I could only nod my head.


“Well, Irvin, they’re hard to resist wearing, I’m sure,” he told me.  “However, since you’ve worn them all night it would be nicer if you put on a fresh pair.  I’ve laid a pair out on the bed for you to put on and leave these in the hamper so I can wash them for you.  You can keep the new pair, too.”


Again, stunned and speechless, I meekly went upstairs to the bedroom and found a very pretty pair of ultra-sheer white nylon brief style panties laid out for me.  The leg openings had about a half inch of sheer white chiffon with a matching band of chiffon atop the waist band and a small pink satin ribbon bow at the center of the waistband.


I quickly stripped out of my jeans and panties, tossing the first pair in the hamper as directed, and then slid the new pair up my legs.  My reaction was the same as when I put on the other pair, and instant hard-on inside my panties.   This pair of panties were slightly silkier and a bit fuller of cut than the others.  I appreciated the double layer of nylon in the crotch as it seemed to caress my cock and balls so sweetly.


Bounding down the stairs, moments later, happy I had such an understanding neighbor and friend, I seated myself on one of the kitchen chairs has Mr. Ferguson outlined our day’s tasks.


Knowing I was wearing his late wife’s panties seemed to bring no notice from Mr. Ferguson and we reviewed the list.  Finally, he grinned at me and said, “If you don’t quit squirming around in that chair the whole world will know you are wearing panties.



“It’s all right,” he went on, “But we’d best keep this to ourselves.  So, be careful, okay?”


I nodded in agreement and delight in his understanding of my new found joy in wearing women’s things.  I was too naïve to know the plan he had in mind for me.


“Do you have a girlfriend?” he inquired as he slid the list of tasks over to me across the table.


“N, no,” I stuttered, “I guess I’m too timid to ask a girl for a date.”


“Well, I’ll tell you what,” Mr. Ferguson replied, “Wearing girl’s things sort of puts you in her perspective and should give you a better understanding of how they look at things.”


No more was said and I was relieved that he had a theory which seemed to okay what I was wearing under my jeans, and my enjoyment of them.


We started back on the windows when I recalled my parents’ plans for the weekend.  Explaining this to Mr. Ferguson caused him to wrinkle his brow, especially when I confessed I really didn’t like going to those relatives.  However, he seemed to accept things and said nothing.


Later on, that morning, I spotted him leaning on the fence of his backyard chatting with my mother who was out picking flowers for a bouquet from her flower garden.  They chatted for quite awhile but I assumed it was just the usual neighborly stuff.


Mom went in the house, at that point, only to return a few minutes later and had Mr. Ferguson a piece of paper.  They talked for a couple more minutes, with Mom nodding her head in agreement with whatever it was before smiling at him and waving a good-bye as each headed toward their homes.


Nothing was said to me until the afternoon ended.  Mr. Ferguson called me into the living room and asked me to take a seat. 


“I spoke with your mother, this morning, and elicited from her your parents’ plans to go away for the weekend.  Further,” he went on, “I got her to inform me how you don’t like going there.


“Well, we’ve struck a deal.  You can stay here, with me for the weekend, and I’ll look after you and we can continue with the windows so the screens will certainly be I place before any warm weather hits.  Would that be all right with you?  I know you’ve buddies you like to get together with, but in this case you’d have to stay here otherwise your parents won’t agree to it.”



“No, no, I’d prefer that Mr. Ferguson.  Really.  I hate visiting that part of the family and I can really use the money,” I admitted not knowing I was falling into trap that I’d soon enjoy.


 “Okay, then,” he rejoined.  “I’ve already told her I’ll need to be in charge and she will remind you of that.  She’s given me authority to take you to the doctor should anything happen but

that seems highly unlikely.  Just as a legal precaution.  You will need to agree to whatever your mother and father insist of you if you want to stay.”


“I’ll do it!” was my happy exclamation.


“One last thing,” he continued, “I will give you a chance to dress fully as a girl since I know you enjoy wearing the panties I’ve given to you.  We’ll set up my late wife’s wardrobe for you to wear but I’ll need to take some quick measurements of you to make sure all will fit.  This will surely help you see things from a girl’s perspective and help you socialize with them.”


So saying, he was soon measuring me from head to toe with a seamstress’s tape and jotting down notes.  As he did he told me girls often take turns playing the boyfriend role with each other at slumber parties which is their great chance to learn about boys.


“So you see,” he said, as he paused to write down some size information, “Girls very often take turns playing the ‘guy’ with their girlfriends so they can learn how to react to boys in the right way.  This will be your chance to do the same thing, only in reverse. 


“There are a few things you’ll need, but not in her wardrobe, that I can pick up from friends in the business, tonight, so they will be ready for you tomorrow,” he advised me.  “You are going to love being able to live like a girl for the weekend and have a better understanding of how they feel about things and this should help you in any future relationships with them.”


I didn’t realize the plans he actually had in mind for me but nodded in agreement and eager anticipation as he took measurements of my body and asked about shoe size, etc.  It was a bit touch and go when he took my inseam measurement, especially with me wearing panties, but I didn’t let myself get too much more turned on.  I wondered if he sensed my hard-on.


That evening, over dinner, I was informed of the plan my parents had agreed to.  I was to stay with Mr. Ferguson who would “look after me” and could not go out with my buddies.  They also reminded me Mr. Ferguson was in charge and I was to do whatever he told me.



My parents dropped me off the next morning with their profound thank you comments to Mr. Ferguson and a note confirming their permission for me to stay with him in case there might be any issues.



No sooner had my parents driven away than I was ushered upstairs and my small duffle bag taken from me. 


 “You won’t need those clothes this weekend,” he reminded me.  “This weekend you get to spend the entire time learning more about how girls are by ‘walking in their shoes’ for the time you are here.  From the reaction you had to wearing the panties I gave you, I’m guessing it’s something you’ve been eager to start.”


Before I could even respond he told me to step into the master bath and strip down to my panties. 


 “Good girl,” he commented, “You are going to be treated just like a beautiful young lady all weekend so that you can better relate to them.  Am I right?”


“Y, yessir,” I muttered, embarrassed as I was indeed wearing the panties just as he expected and sporting a hard-on inside them.


Without another word he set about double checking some of the measurements he’d taken the day before.  When he double checked my leg inseam my cock throbbed inside the panties and he laughed softly.  “Don’t up and cum on me,” he muttered as he knelt between my legs as he held the measuring tape, “I know wearing panties excites the girl in you.”


With that he stripped the panties off me and had me step out of them.  Then, taking an electric razor, he clipped my pubic hair close leaving a longer vertical patch at the top center of my cock.  This is exactly the same pattern a lot of girls grow naturally that men cannot since men are always an inverted triangle of pubic hair as are most of the girls.


I was shocked at his doing this, but knew he was in control and I found this stimulating.  Next he directed me to slather a lot of goo on my legs and underarms as well as my chest.  With a different goo (I later learned this was all Nair depilatory) he carefully, and gently, did the area around my cock and balls before coating my balls liberally with the stuff.   His applying the goo to my cock and balls was a terrific turn on and I was soon sporting a very stiff hard-on but he didn’t comment.


“Now stand still on that towel and don’t move until I return,” he advised and left the bathroom.

I found myself holding still in one place for about 10 minutes before he came back.


“Good girl,” he said again, causing me to blush, “Now take a nice warm shower and be sure to rinse all that goo off of you.”



I did as told and was astonished to find my body hair, which had already turned all crinkly, begin to slide right off of me and go down the drain with the shower water.


No sooner had I finished than he opened the shower door and had me step out onto the towel once again. 


“Now stand still again as we begin your transformation.  You realize you will dress only in girl’s things and be treated totally like a desirable young woman all weekend until you have to go home.”


“Yes, sir,” I admitted meekly and wondered what was next and why did I agree to this.


“Good,” he responded curtly and then toweled me dry before powdering me from neck to toe with a soft coating of light talcum.


“I’m going to help you dress, this time,” he informed me, “And from then on it will be up to you.  So, you had better pay attention to how girls dress themselves.”


With that he had me put on a soft pink satin brassiere by clasping the hooks in front of myself and then sliding it around my midsection until the hooks were properly in the back and I could slip my arms through the straps that were to go over my shoulders.


Next, he produced two silicone breast forms with stiff nipples that protruded a good ½ inch and helped me fit them into the cups of the bra I was now wearing.  I was amazed to look down and see the view girls saw constantly when they looked that direction.  I loved the look!


Next came a garter belt and it was put on in the same manner, except the straps hung down with little garter tabs at the ends.  Directing me to the bed, in the master bedroom just steps away, he showed me how a girl puts on her nylon stockings.  In my case they were a pair of

Seamless RHT evening dress sheer flat-knit Hanes nylon stockings labeled “Barely Black” and very sensual, silky, and shiny. 


The feeling of the nylon stockings on my now hairless legs was incredible and not something I was quite prepared for.  Wearing panties had been terrific but stockings felt soooo much more silky and damned stimulating on my legs.


“Okay, now stand up and put on the panties laid out on the bed for you.”



I knew how to put them on, of course, but nearly fainted as the wispy sheer pink nylon flare leg panties slid up over my nylon stockings.  I don’t know if it was the nylon material or the soft

lace at the leg openings that enhanced the sensation but by the time I had them in place my knee caps were bouncing up and down inside my stockings and I was about to faint.


 “Easy there, dear,” he muttered putting a reassuring arm around my waist and held me to himself so I wouldn’t fall down, “This is really stimulating you, isn’t it.”


“I’m, I’m sorry, Mr. Ferguson, but the sensations are more than I expected.”


“No problem and you don’t have to apologize.  After all we both agreed you needed to learn this and it is a learning curve for you.  However, your panties are tenting out in front in a most unladylike way.  We need to take care of that.”


No sooner had he said that than he slid my panties down to my knees and began stroking my cock !!


“Do you want me to stop and let you do it, or do you want me to continue?” he whispered in my ear.


“N, no, no, don…, don’t stop,” I managed to stammer in reply, being too turned on to refuse.


He was expert with his hand and soon I was nearing the feeling I was going to cum.  Suddenly, his fingers encircled the base of my dick and my balls squeezing hard as he said, “I will be in total control of your body this weekend if you want to learn about girl’s reactions, understood?”


All I could do was nod “yes” in response.


“Do you want me to make you cum?”


“Pl, please, sir, yes,” I stammered.


“You want me to make you feel completely like a girl, don’t you?”


“Ye, yes sir,” I muttered again powerless to do anything.


“Then I will have to assume the role of your boyfriend so we can do that and you will let me be your boyfriend, won’t you,” he told me as he slowly began stroking my cock again.


“Ye, yessir,” I weakly gasped as he began working me up to a cum.


“Then you will have to do certain things for me as if you were the girlfriend to me.”


“Yessss,” I wheezed as he kept massaging my dick that was crying out to cum.


“Good, then it is agreed,” he muttered as he suddenly dropped to his knees and engulfed my cock in his mouth and began sucking me off.


All I could do was moan and place my hands on his head as he worked on me.  It only took him a few moments and I was gushing forth my cum into his sucking mouth.


After I could finally spurt no more he stood up and kissed me fully on the lips.  I was so weak from what he had just done to me I could only lean against him and let him kiss me.  When his tongue pushed its way inside my lips I could taste my own cum that remained in his mouth.


Before I realized it I was returning his kisses and found myself liking the taste of cum and being kissed by him.


“You’re going to love being a girl,” he said as he slithered my silky pink panties back up in place.


“Now,” he told me, “We’ve work to do around here and you have to earn your keep, young lady.  By the way, what girl’s name would you like for me to call you?”


Still caught up in the moment of it all I could think of few but did mutter I liked the name Alicia.


“Excellent, Alicia.  That is what you will be called whenever you are here from now on.”


He found a pair of long pink nylon panties and my look of curiosity made him comment, “These are called panty liners and a lot of women wear them under their slacks.  Can’t have you working outside the house in a skirt and blouse or dress, just yet.”


I wondered what he meant by the “just yet” wording but stepped inside the long panty liners and was thrilled with the feelings of another layer of nylon sliding up over my stockings and panties.  Then he helped me put on a soft pink nylon camisole with scads of lace across the top of the bodice and satin straps over my shoulders.


Next came a plaid shirt, or so I thought.  He let me put it on and then I noticed a touch of lace at the cuffs of the short sleeves and that the buttons were on the wrong side. 


Seeing my dilemma, he told me, “Girl’s things have the buttons reversed from men’s.” 


Next he handed me a pair of navy blue slacks and it was a surprise to me to find the zipper was on the side and not the front.  I immediately understood he was having me wear only feminine things.


A pair of black leather “flats” were handed to me and I slipped the soft shoes on my feet.  It was a surprise how easily they slid on over my nylon stocking clad feet and felt instantly very comfortable.


“Good,” he said, adjusting my longish hair to make it full down around my face and not be tucked back behind my ears as usual.  “It looks like you enjoy this and we’ll address putting make up on you later when you won’t be outside.  Don’t want to embarrass you by having anyone notice you are a boy wearing only girl’s clothing, do we, Alicia?”


Before I could reply he was leading me downstairs and we were soon at work storing the last of the storm windows and putting up the screens.  With him helping me, this time, it went twice as fast as before and by noon time we were finished with the whole house.

“Good job, Alicia,” he said softly as we put the ladder away in the garage and headed into the house for lunch.  “You’ll be able to change into some other more comfortable things after we’ve had a bite to eat and this afternoon will be less man-like labor.”


“Gosh, Mr. Ferguson, I feel a bit odd dressed like this but these clothes are much more comfortable to wear than I thought.”


“I knew you would like this, and I can see a bit of a resurgence tenting out the front of your slacks again.  Am I going to have to give you another ‘treatment’ like I did before?” he asked.


“Oh, I, uh, I,” I tried to reply as we walked through the house and he now had his arm around my waist holding me closely to him, “I like, I liked that a lot, but is it right?”


“Alicia, Alicia, Alicia,” he said with a bit of frustration, “We agreed if you are going to learn how girls see things you need to live exactly as a girl for the weekend and I must play the role of your boyfriend, just like girls often do at slumber parties and such.”


“Yes, yes sir, I remember.”


“Good, now before we have lunch let’s slip upstairs so I can take care of that growing problem inside your panties.”  By now I knew what was coming for me.



Inside the master bedroom he helped me out of my blouse, shoes, and slacks before lowering my panty liners down my legs and teasing me as he did so.  Then he slipped the wispy panties down over my nylons and my cock stood at full attention.


Kneeling before me he stroked my cock a couple of times and fondled my balls with his other hand.  Then he leaned forward and kissed the head of my cock and then engulfed it fully down to the base in one motion with his mouth.  I’d never had my cock sucked before, and now I was having it done to me for the second time in just hours!


I remember him sucking on me and I was going crazy over the sensations and knew he would soon have me spurting cum into his waiting mouth again.  I was already wondering if he would kiss me and let me taste my cum juices on his lips and tongue.


Suddenly, he stopped and once again held my cock and balls in a tight grip preventing me from cumming even though I was so close.


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