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My step mom Diane and I had not really gotten along very well, but as we were both very sad, mutual consolation had brought us much closer. It was probably 6 or seven months after the funeral when our relationship changed drastically. I had resumed my cross dressing habit. My weakness has always been pantyhose. For as early as I can remember (three years old), I have been sneaking hose out of the laundry and wearing them.
Diane had the perfect closet to borrow from. She was 5’9”, 170lbs, and ample D-cup breasts. She always wore suntan hose, even under jeans and sweats on the weekends. On my luckiest days, she would ask me for a foot rub. Getting that close, the feel of the nylon, peaks up her dress at her sweet pussy, it gave me a raging hard on every time that I would futilely try to hide as I scampered up to my room.
Well, it happened one morning. I was finally caught. I guess I always secretly wanted to be caught. Such a thrill when you’re standing in front of a full-length mirror, dressed to the nines, your heart racing as you listen for the first sound of a car pulling into the drive.
On this particular morning, I was still wearing a pair of her hose from the previous night’s girly time when Diane came into to wake me up. Apparently I had kicked a leg free from the covers in the night and when I awake it was to the sensation of her hand sliding up and down my calf. It took me a while to fully grasp the situation. She was smiling sweetly as the panic washed over me.
I started stuttering excuses, but she shushed my and patted me reassuringly on the calf. “It is fine, don’t cry. I like pantyhose so how can I get mad if you like them too?” she asked.
“But you do need to get up and started on you chores. I have a meeting with my professor in an hour, so you’ll have the house to yourself this afternoon. I need you to do me a favor and get the laundry all caught up,” she said.
I replied that I would, still numb from the fact I had been caught. I was only now taking in the fact the she still rested her warm hand on my calf. She was wearing a long navy sundress with wedge sandals as well as the obligatory suntan hose. She always looked well put together. Today was no different. Her brownish auburn hair was shoulder-length and permed in a rather 80’s type fashion but she pulled it off well.
I also realized my hard on was tenting the blanket despite its hose restriction. She just smiled again and said that it was perfectly natural considering all the nylon in the room. She leaned in to kiss me good-bye and ever-so-slightly brushed her hand over my dick in the process. She kissed me warmly and told me she would see me in a few hours.
I put on a pair of shorts over my hose and a t-shirt and headed down to the kitchen just in time to see her pull out of the drive. Next stop was the laundry room to see what I was in for. Not bad, only a few loads of her school clothes. The t-shirt and shorts were promptly swapped for a jean skirt and a cashmere top that were near the top of the hamper, and I wandered my way into her bedroom once the first load was under way.
The next selection was a pair of 3 inch, blocky Mary Jane’s that she had bought for last Halloween when she and my dad had gone as punks to a costume part. The tent on the front of my dress was quite evident as turned in front of the mirror.
The ring of the doorbell almost stopped my heart. From where I stood, I could see the eyes of my neighbor, Mr. Johnson. He smiled and motioned be to come to the door. As I shakily opened the door he politely told me that our garden hose was leaking so he had installed a replacement.
I quickly thanked him and asked how much did we owe him, whereupon he smiled broadly and said “how about a glass of lemonade.” It was a warm September so by chance we had some on hand so I eagerly agreed to comply with his request, almost forgetting the way I was dressed until my nylon thighs started to swish as I attempted to walk in my heels.
To be honest it was not my first time in them, so I think I did a pretty good job. It is not until you have someone’s eyes following you do you realize how much those make your ass move when you walk
I got the glass and the pitcher from the fridge and offered Mr. Johnson a seat at the table. He was in his mid forties, in good shape, 160 lbs and 5’8. He had a runners body and was in fact wearing a blue jogging suit today. He accepted the glass from me and bade me join him. I did as I was told, sitting down in the dining room chair next to his, and as I crossed my nyloned legs, he complimented me on them and said he like my style.
With that he reached out and started stroking my leg. I moaned as he squeezed my thighs working is way up under my dress. My hand started to do some exploring of its own, tracing their way up his thighs and to his swelling cock, tracing its outline with my fingers through the slick material.
Mr. Johnson then pulled me onto his lap allowing me to grind my pantyhose and cashmere against him in the most amazing of sensations as the two materials moved back and forth. He leaned in and kissed me lightly, and suggested there might be another favor I could do for him in addition to the lemonade.
He then guided my hand to the waistband of his tract suit. I had seen it in the porno movies but had never sucked a dick before. Fantasized sure, but as I descended to my knees pure ecstasy washed over me and I lusted to get him in my mouth.
I gingerly inserted my fingers under the elastic and coaxed the pants down, revealing a lovely 5-inch cock with a bulbous head. He had nice large balls too, and that’s where I launched my attack. I leaned in to lick and suck on one while his semi-hard cock rested across my face feeling very warm and pulsing. He moaned and placed a hand on my head to encourage what I was doing.
After taking my time working on both of his swollen eggs, I cradled them with my hand as the other manipulated his cock so I could lick and kiss every inch before taking him in my mouth. In under a minute his balls were surging in my hand as he pumped his down cum down my throat. Missing only a bit dribbling down my chin, I lifted his pants back up and smiled up from my submissive position chasing the errant drop with my tongue.
Mr. Johnson thanked me and said that was one of the best blowjobs he had had. I was beaming with pride as I walked him to the door. He kissed my lightly before he made his exit.
My cock was rock hard as I returned to the laundry room to resume my chores and lust over what I had just done. A pair of high-cut, sheer black briefs caught my eye as I was folding. I rubbed them on my dick for just moments before knowing I needed to try them on. I slid them into place and only started rubbing my budge when I heard the Diane pull up. Frantically I took off the borrowed garments, still giddy at the fact that I was wearing her coffee colored hose under my shorts and she wouldn’t even be mad at me for it.
I greeted her at the door noticing she looked a little flushed and flustered. I suggested she sit on the couch and I would get her a glass of wine. She agreed and related the afternoon’s meeting with the professor. He came on to her and she felt helpless to say no as he held so much of her future in his hands so she gave him a blowjob. She asked me if I knew what a blowjob was. I feigned a lack of knowledge despite this morning’s adventure with the neighbor, so she explained the act in detail and before she was through I was thoroughly aroused listening to her talk so dirty.
She then explained that had blowing the professor left her hot and bothered, so she had invited him to dinner in the hopes of getting righteously fucked. The professor was from South Africa, and very conservative. I said it was no problem; I could make myself scarce.
“No wait there is more,” she said. “In my cubicle, he saw a picture of you dressed up for last Halloween as a princess and said he was looking forward to meeting my daughter.” I blanched. Halloween has been mine and many other gurls only chance to crossdress with impunity. Last year I was Dorothy from the Wizard of Oz, somewhat because my step mother is a huge fan, but mostly because I wanted those red sequined Maryjanes.
“I can’t tell him you dressed like a girl last Halloween. He would totally freak out, and I really need to make him like me. His class is the hardest I’ve taken and the last one to complete the degree,” she said.
I feigned reluctance but agreed to do anything to help her. She smiled broadly and said “well you are already pretty hairless so I guess we can skip the shave.”
“I stopped and picked you up some things, not that mine wouldn’t fit you, I’m sure you look great in them,” she said with a wink, “but I thought this would be more age-appropriate.”
Out of the bag came a red-plaid schoolgirl dress, a black sweater, black ballet flats, and a pair of suntan crotchless hose that were probably 40 denier and very shiny. She also produced a waist cincher and and a pair of sheer black bikini briefs.
I had the items on in no time flat, and was back in the mirror admiring myself. Diane was beaming at her excellent fashion choices as she smoothed the dress over my body sending thrills done my spine. I turned to face her but the clock in the living room struck five breaking us out of our reverie as the hour of his approach was nearing. She sat me down at her boudoir and brushed my medium length blond hair out of my eyes and affixed it that way with a large red ribbon that matched the rest.
Eyeliner, eye shadow, blush and lipstick rounded off the session, and again she beamed as she spun me around to see my reflection. I gasped. Staring back was a cute, slightly chubby, blonde girl. I thanked and kissed Diane, careful not to smear the lipstick.
She said she was happy I was happy and thanked me for helping out tonight. She ordered nice Italian takeout and we left to pick it up. Walking outside fully dressed was amazing. The wind up my skirt tickled so sensuously as I walked to the car and got in as demurely as possible.
In our hurry to get back, a cop pulled us over for speeding, but luckily only gave us a warning. He smiled broadly and said we both look very pretty. He looked back at the address on Diane’s driver’s license and said he lived just two blocks over. “Maybe I’ll see you around sometime in less formal circumstances” he said looking back to me with wink. Diane noticed the gesture, and teased me once we were back on the road.
We pulled into the driveway with 15 min to spare. The doorbell rang as we were just finishing setting the table. Diane met Mr. Okafor at the door and I saw form the kitchen they shared a long, deep kiss at the door. I was introduced to a black man, probably in his mid-fifties, wearing a clearly expensive suit. He was six-foot with a shaved head and slightly rounded belly. He leaned forward and kissed my hand as he passed, causing me to blush.
He smiled warmly and produced a bottle of wine to compliment the dinner. Diane opened it and poured three glasses. I didn’t like the taste very much, I finished it over the course of dinner. We retired to the living room and Diane put on a movie. Some historical drama related to their field, but pretty soon I was bored and excused myself to the restroom to check out my make up.
Upon my return I noticed a blanket now lay across the two of them. I returned to the couch close enough to share some blanket and noticed movement near Mr. Okafor’s crotch. Out of the corner of my eye, I confirmed that my step mom was rubbing her professor under the covers. A shock hit me as he started rubbing my leg.
I looked at Diane who shot back a mischievous grin. Her rubbing became more deliberate while she looked me dead in the eye with lust. Mr. Okafor moaned and put one of his arms around me. My hands went out and met Diane’s on top of a prominent bulge.
“Remember what I told you about this afternoon? Wanna try” she asked wryly. I leaned in closer and kissed her, only breaking long enough to whispering a soft “yes,” before kissing her glossy lips once again. She pulled back the covers and both of our hands worked in unison to free his cock. To Diane’s delight and my astonishment, a thick eight-inch, uncircumcised cock now throbbed in our hands.
Remembering what Diane had taught me, we leaned in and went to work on his beautiful cock. Up and down, we brought our lips and tongue in unison on either side of the throbbing member. She was the first to take him into her mouth, so I slid down and went to work on his ball swith out breaking eye contact with my step mom. I could see Diane had her hand up her skirt and was aggressively rubbing her pussy as she sucked him off. Once he was fully erect at a solid nine-inches and very thick, Diane poked a hole in her pantyhose and swung her leg over him while slid to my knees front of them.
“Would you give me a hand, Michelle?” she cooed has she seductively wiggled her ass over his cock. I Reached out and guided that monster into my step mom, and she sank down upon it with a moan. From my position her beautiful pantyhosed ass was right and front of me, so I enlarged the hole in the hose slightly and buried my tongue in her ass.
Diane was moaning loudly as Mr. Akafor pushed into her from underneath and his balls came to rest at my chin. I alternated my attention between the two lovers all the while running my hands over her thick legs and ass. After five minutes hey came together. I had one of his balls into my mouth when I sensed the rhythm change, and he moaned loudly as he blasted his cum deep into her well-fucked pussy. Once they caught their breath, she dismounted and suggested I clean our guest up. I obeyed, sucking their intertwined juices off of his semi-flaccid cock.
I then moved over to her. She pulled my head towards her pussy, the nylon on her legs sliding sensuously along my face as I dove in, eagerly sucking on her clit and lapping at the labia at he ran out of her. Her orgasms was violent as she ground herself against my mouth. She tasted amazing and I was proud of helping to satisfy her.
I went to the bathroom to get towels and touch up my make-up. We got cleaned up and Diane got everyone another glass of wine. Mr. Akafor thanked up for our hospitality and suggested next weekend he would host us and I could meet his son
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