This is a work of fiction unlike another entry of mine.
I would love to get feedback from any and all readers, but especially from older women and men with desires for young men and boys who like to wear feminine attire. A woman that loves to do something special for her spouse or boyfriend is a person I would love to hear from.......and of course the lucky spouse or boyfriend too.
This begins as I live in a neighborhood close to a couple in their late 40s or early 50s. My name is Alan and I am a 16 year old boy and my neighbors are Steve and Liza Lennon. I am an only child and the Lennons do not have any children which I suppose is why they take to me as much as they do.
Our neighborhood is well to do and the Lennons have a pool. During the summer between my 10th and 11th grade I spent time there doing odd chores for spending money. I would mow grass, weed, clean the pool, and other odd chores as they came up.
Mr Lennon's job took him out of town frequently and I loved the chances I got to spend with Mrs. Lennon. She was very beautiful though would often say as many women do that she was overweight. Maybe 10 pounds, but I didn't think so at all. She had beautiful legs on a pretty figure, but her most endearing quality was her beautiful face and gorgeous sexy, full lips.
She was someone I could talk to normally about everyday things unlike other people her age and parents. She was really cool.
I tried to be sly about it and I would glance at her often and hope she didn't notice me doing this. I especially liked to watch her apply her lipstick and other makeup and truly hoped she didn't catch on. We got along great and she was a little like a second mom so I didn't want her thinking I was a pervert or something.
I had sneaked into my mother's closet numerous times and tried on clothes and shoes and then would try on different makeup. I loved the smell of women's clothing and the smells of lipsticks and makeups and was always fascinated with it all. Mrs. Lennon was so pretty just like my mom so I knew she would have lots of pretty clothing. She worked for some lawyers and always dressed nicely, but I was curious about what kind of lingerie she had and what kind of makeup she wore.
I wish she had kids so I would have an excuse to go in their house more often, but most of the chores I was hired to do were outside. This changed one day when she called and asked that I come over while she was at work and clean the gutters over their garage. She said that Mr Lennon was out of town and that this chore needed to be done. I eagerly went over and set to work. Maybe this would be a chance to peek in her closet if I got up the nerve.
It was maybe mid morning when she pulled up in the driveway. Fortunately I was working on the roof and had not gotten up the nerve to sneak in and this was a good thing. She smiled up at me and said that I should join her on their deck in a few minutes after she changed and got some Cokes.
I wished she wouldn't change from the gorgeous outfit she was wearing which was a medium length business suit with gray heels and stockings. I got hard just staring down at her, but she didn't seem to notice and went right inside.
I climbed down and went to the deck with sweat pouring off of me on the hot summer day. She came out a few minutes later and my hard on sprang back to life as she was wearing a tight sleeveless white top and very skimpy pale blue shorts with trim to match her top. To show off her legs she had on some medium high wedge sandals which kept my attention for awhile longer.
"Do you like my new sandals Alan. I see you staring at them and I just bought them on the way home from work." I told her I thought they were very nice, but I'm sure my tented shorts gave that away. I just had on shorts and sneakers and she was looking at me also.
"Here, have a Coke Alan and cool off. You are all sweaty and maybe I shouldn't have you working on the hot roof today." I told her it was ok and that I was nearly done anyway. "Why don't you quickly finish then and come inside for a more reasonable chore. I don't want you fainting and falling off the roof now do I?" We chatted another minute or two as I finished my Coke then I went back to the roof.
I quickly finished as I thought about little else but her gorgeous tanned legs and her ass in those shorts. The sandals were perfect and I would have loved being the salesman helping her try them on. I gathered my things and climbed off the roof and put the ladder away.
I walked into the house and found Liza at the dining room table with several small containers in front of her and a little mirror on a stand. She offered me another Coke which I accepted and I hadn't noticed that she put some drops into it. I drank part of it as we talked and she put on a makeup show for me. I have always loved watching women apply makeup and especially lipstick. I mentioned earlier that one of her finest features were her full and beautiful lips. I didn't want to stare, but I couldn't help looking up often as she applied various things.
When she got to her lipstick she looked at me and asked a question that embarrassed me slightly. "Alan, I have noticed at times that you look at me when I'm doing this and I don't just mean right now, but other times." It was true and I must have looked a little sheepish right then, but she just winked and said she was flattered that I looked. I was feeling a little funny about this time as the effects from the drug she added to my Coke were kicking in and it put me at ease. I liked talking to Mrs. Lennon as she was very cool.
She continued applying makeup and one she got to the first tube of lipstick she began a more serious tease. "Tell me something Alan, since you seem to be so interested in watching me I can only assume that you have done this yourself. You've worn makeup haven't you dear?" Since the drug was allowing me to be so loose lipped I told her that I had tried on my mother's clothes over the years and her makeup too. She asked what I liked to wear and I told her mostly lingerie, shoes, and lipsticks as my mom had dozens of types and colors.
Liza smiled and reached over and pinched my cheek then lightly kissed the same cheek and said "we are going to have so much fun." By now the drug was taking it's full effect and I was enthralled by her every word in anticipation of what was coming next. She applied a small amount of blush and then a hint of eye shadow. I watched with delight as she did this as the times I did it I tended to cake it on and it looked trashy. I could learn a lot if I paid more attention and quit squirming from the hard on in my shorts.
The color was a light blue and it looked beautiful as it closely matched her pale blue shorts. She then asked that I pick a lipstick color for her. "Since you watch me do this you must have a favorite color honey so please pick one that will me me sexy." "I think they would all do that" I boldly said since the euphoric feeling had removed any inhibitions. I pointed to a long thin tube called "Summer Peach" and suggested that one. "That is one of my favorites, you are so flattering."
She pulled the top off and rolled it across each lip very lightly then purse her lips together. "Is this how you would do it sweetie?" I said yes, but that like the eye shadow I usually put too much on. "I always roll on a lot because I love the act of applying it and the smells and feel of the creamy cosmetic."
She put a little more on then picked up a little brush and a tin of a similar color and brushed on some more. It was a little brighter and highlighted her full sensual lips and she pursed them again and blew me a kiss. The final tease was found in another tin and she dipped another tiny brush into it and applied some very shiny clear gloss and expertly distributed it evenly. Her lips now looked as though they had a fresh coat of wet paint and were a delicious shade of shiny peach.
"Do I pass your inspection my pretty little thing?" My head must have almost come unscrewed I nodded yes so vociferously and I stuttered out "oh yes you look gorgeous." She winked and blew me another kiss then teased her tongue across her teeth and around her lips in the most sensual manner. My dick could hardly take the strain.
"My pretty young thing looks so anxious would you like me to try this on you?" She stared at my almost hairless legs as she said this and before I could tell her yes she was dabbing an apricot color onto my lips. "I just wanted to get an idea and I thought this would work. You are so unbelievably cute that anyone would love to play with you." She got up and walked over and took my hand and we went back to her bedroom. I had never been in there, but my fantasies were coming true as it liked like what I guessed. Very feminine and it smelled of sensual perfume.
The perfume scent and the drugs made for my being very amorous and I was complete putty in her hands. The room contained a make up table with a large mirror behind it then a bed across the room from the table. Against the wall was what looked to be a pedestal maybe 12-18 inches high. A chair with some outrigger type bars with straps took up a corner. Otherwise it was the typical feminine room.
She took me into her bathroom and ran a bath with some sudsy bubble bath and asked me to remove what few clothes I had on. She admired my stiff dick for a bit and lightly kissed the head then guided me into the tub. She took a soft cloth and bathed me from head to toe paying a lot of attention to my dick and to my legs. She shampooed my hair, rinse it then rinsed me and I got out of the tub where she gently patted me dry.
"If I do something for you honey would you do something for me, anything I ask?" Before I could respond she put her glossy mouth up to my dick and licked the precum off with a quick flick of her tongue. She then placed her mouth slowly over the swollen head and lightly sucked. She went gently and slowly at first then applied more pressure and took more in each time as she lightly pinched the base of my dick with her manicured finger and thumb. Her other nails teased the underside of my sac and she continued to vacuum my dick into her mouth.
At this point she backed off long enough to ask "I never got your answer sweetheart, would you do something for me?" I told her I would do anything she asked of me and she smiled wickedly "Would you really do anything anything I asked?" I could hardly contain myself as she put her heavenly mouth back onto my throbbing dick and sucked with more pressure for about a minute until she released her thumb and finger where I exploded hot semen into her mouth. She kept her action going on my partially hard dick and seemed to enjoy swallowing my cum and licking the rest as she lubed my shaft with the hot cream.
She moaned and cooed and soon had a finger probing my ass at which time she asked that I follow her into the bedroom. I was like a puppy as I trailed her with nothing but an open and stained towel keeping me from total nudity.
When we reached the bedroom she ushered me into her large walk-in closet which was like my dream come true. There were countless dresses and outfits, many that I'd seen on her and many that I had not seen. There must have been 50 pairs of shoes in every style imaginable. The scent was hypnotic and she went about picking out something for me to wear.
"First, you're getting into this little romper and I do hope you'll fit into a pair of mules." The pale yellow romper fit very nicely and she snapped together 2 flaps in the crotch. She pulled a pair of 4 inch high white mules and they fit perfectly. I walked the short distance inside her closet to which she said "have you been in here before trying things on you naughty little girl?" We both giggled and I assured her I had not, but always wanted to. She giggled again and herded me out to her bed.
She pulled the strange chair with the outriggers over and placed in in the center of the room and instructed me to sit in it. It configured me as such that I placed my ass into a low seat then spread my legs up and onto the outriggers. I really didn't know what she was doing other than I loved her careful and calculation attention as she placed the heels of the mules into little pockets. She didn't put the straps onto me and I could easily remove my feet if I wanted, but why would I want to?
She brought over a small basin with warm water in it and a feminine razor. I was facing the large mirror across the room so I could see myself. My legs were not all that hairy anyway, but she insisted we have some fun and besides "you said you would do anything for me didn't you love?" I nodded approval and she went on "you have such well shaped legs and once we get this unsightly hair off of you they will look gorgeous." I let her go about her chore as she sponged off one leg, applied a little shaving lotion and began to shave me in long careful strokes. The hair fell onto a towel on the floor.
She shaved each leg in the same careful manner then rinsed and wiped off the excess lotion and hair. "Look into the mirror sweetie and see your admirer as you are becoming quite pretty and sexy." She blew a seductive kiss towards the mirror and went and got a little bottle from her dresser.
The bottle contained baby oil and she poured a little on one leg and with a soft cloth rubbed it all around my legs. She added more so that the entire leg was coated then she did the other one the same loving way.
"Let's give our mirrored admirer a little look at what's tenting your romper" and at that she undid the two snaps holding it together and my dick sprang out and pointed at the mirror. She got a clean dry cloth and buffed my legs to a shimmer then any excess on the cloth shined up my dick as well. I was ready to have my photo taken for a porno mag it looked like.
She walked to one side of me and began applying make up, first blush, then eye shadow, then the most beautiful lipstick in an expensive looking tube called "Rose Porcelain". It was a similar peach shade as hers but didn't have the same cum stain on it. She finished her ministrations then went behind me and teased out my hair.
This went on for some time and I could see her reflection in the mirror as she smiled continually towards it. My hair was long and now with mousse and other gels added to it was a pretty and thick style. She added ear rings and a choker as well as a bracelet and anklet and I looked very complete.
I was stone hard again as I stared at my reflection and she too continued to gaze into the mirror. She went to a dresser drawer and brought back a pair of silk panties and said "would you love to have some naughty fun my darling? May I call you Ellen now that you're as pretty as I knew you would be?" I simply nodded as she wrapped the silky panties around my dick and began to stroke me into bliss. In no time at all I came into them and she gave me the most sensuous kiss of my life.
"Don't go anywhere darling and I'll be right back, but don't leave our friend idle" as she stroked my dick and smeared it's hot cream around. She disappeared for a little while and I was left to wonder and revel in my good fortunes. I stared at myself in what she had called my "mirrored admirer". What had she meant?
What I didn't know was that Mr Lennon was not away at all but rather here the entire time and restrained in a small closet behind the mirror. It was a 2-way mirror and he was watching everything going on in the bedroom. He was gagged and the poor man had sweat pouring off of him from the tension of watching his wife's naughty game.
She took the cum soaked panties and placed them over his head. She removed the gag from his mouth and smeared my cum around his face and hungry mouth as he moaned with pleasure. They both looked out through the mirror where I was in my displayed position for them stoking myself to unknowing eyes. I rubbed my polished legs then back to my dick and was in ecstasy.
Behind the mirror was a similar story of ecstasy as Mr Lennon was near exploding as Liza massaged his huge cock as he strained in his chair.
"Happy birthday darling now do you want me to fuck my lesbian lover or do want her first?"
Please send any feedback as I'd love to hear from you.
Kisses, Ellen XXOO