“Well I think it’s a great idea.” Said my girlfriend Cheryl after bringing up the topic during dinner. It was a month before the “Walk a mile in her shoes” support parade against abuse of women. “What kind of example would it be if my own feminist boyfriend won’t support me especially at WFS?”
Cheryl worked as an executive officer at “WFS”; a women’s financial support company. There were a number of male workers but mostly were lower managers or office workers. The upper execs and the other employees were women and as such, her office was in total support of these type of causes. Actually this was where I met Cheryl. We became an item and to ensure there was no conflict of interest, I left. Cheryl made sufficient money that I could stay at home to start my own web design business.
“Of course I support you. Yes, I’ll do it.” I answered reluctantly, not like I had a real choice in the matter. Once she gets something in her head, there is no getting around it.
“Oh thank you, Jerry! It means a lot to me and the company.” Cheryl kissed me. “Especially since that bitch Lori is already bragging she can pull in more money than anyone else! We’ll show her, won’t we?”
Again I reluctantly agreed.
“Besides, you know I love shoe shopping too. We can go get you a pair this weekend so you can practice.” Cheryl told me. “Practice makes perfect after all!”
I guess the good thing agreeing to Cheryl’s “request” resulted in phenomenal sex that night. She wore my favourite red baby doll nightie with crotchless panties that never failed to get me rock hard. She took my five inch bone totally into her mouth and soak it thoroughly before she sat cowgirl on me. Not that she needed any lube. Cheryl was so wet, I slid inside her easily in one go.
Her cunt was so hot; so tight I came in less than a minute.
“Jesus Jerry! Can’t you hold on longer than that?” Cheryl admonished me at my very premature ejaculation. I tried to apologise but she told me to “Shut…Up…!”
She moved herself over my face and planted her cunt on my mouth. “Clean me!”
I used my long tongue to lick out her fuck hole. I may not be big; I may not last long but I can erupt like a Mount Vesuvius and spew huge amounts of lava. Launching my mouth missile into her was like blasting apart a dam. The tsunami of cum and pussy juice flooded into my mouth. I swallowed as much as I could but ultimately failed.
Cheryl face fucked me until she came a number of times and fell off of me exhausted.
Saturday came quickly. Another round of premature emission and face fucking left me and my tongue spent. Cheryl was full of energy. I showered to wash the crusting sex juices off my face and sat down for a cup of coffee, but Cheryl was already ready to go. She was sharply dressed in a white silk blouse with a mid-thigh black skirt. Although she wore stockings, I could see her red painted toe nails through the peep-toes shoes she had on. She was more than two inches taller than me in bare feet, with her pointed heels on, she was almost seven inches taller. “Get dressed and let’s go!”
I pulled on a red polo shirt and some loose khakis, but when I went to put on some white sports socks, Cheryl stopped me. “You can’t wear those when you’re trying to buy shoes. They won’t fit properly.”
Cheryl dug through her drawers and threw something at me. I unballed it and held a knee high nylon stocking in each hand. I started to protest. “I can’t wear these!”
“Well, would you prefer to wear these?” Cheryl asked in a tone that wasn’t really a question. She pulled her skirt up to show me she was wearing proper stockings and garters. Cheryl always detested pantyhose. “Besides those look like regular guy socks so no one will think you’re a girl.”
I put them on then Cheryl made me wear some dress shoes rather than the sneakers I was going to wear. I didn’t want to tell her, but had to admit the socks actually made my feet feel pretty good.
We visited a number of stores at the mall before she selected a pair for me. They were red velvet, peep-toed pumps with a slight platform. A strap went over the arch of my foot and another around my ankle secured the shoe. Even with the steel spike heel, I was still an inch shorter than Cheryl.
Normally Cheryl would spend the rest of the day dragging me around shopping, but she was too excited and wanted to rush home. I barely got through the door before she stripped me naked but for my knee highs and new shoes before she ravaged me relentlessly. It didn’t matter how fast I came, she continued to fuck my half wilted cock until it was red and raw. Of course she made me finish her off with my oral probe.
It was Sunday by the time we had enough energy to get up. It wasn’t long before Cheryl had me trying to stand in my new shoes. And just my new shoes with my stockings of course. It was very wobbly at first. Trying to balance without twisting my ankles was more difficult than I thought it would be considering how easily I’ve watched Cheryl and other women walk or even lope in heels.
With a little help, I managed to take careful steps forward. “Cheryl. They’re too tall! I can’t keep my balance.”
“Well, now you know what it’s like to walk in women’s shoes.” Cheryl smiled. “You’ve stretched your knee highs and they are snagged, saggy and falling down. Keep practicing.”
I stumbled around while Cheryl left. She returned a few minutes later and handed me some things. A black garter belt and stockings. “You can use these until you get your own.”
I looked at her confused. “You want me to put on your stockings and garters?”
“Well it’s better than walking around with saggy elephant ankles! At least the garters will keep your stocking from falling. I’m not giving you a pair of my stay-ups.” Cheryl told me with hand akimbo. “Take off your shoes and put those on!”
I unbuckled my shoes and removed them along with the stretched out socks. I donned the belt and hosiery as instructed by Cheryl and rebuckled my shoes. As I stood, the tight feeling around my legs was euphoric. I guess Cheryl noted it too. “I think you like wearing stockings!”
My little boner had sprung back to life and pointed directly at my girlfriend. Cheryl dropped to her knees and sucked at my erection. “God that feels so good, Cheryl. You’re going to make me cum again!”
With that warning, my cock to pop from her mouth. She used her hand to lift it up so she could mouth my testicles. She took both of them into her hot mouth and swirled them around. I spasmed at the sensation. She had me turn and part my legs. With one hand, she started to stroke me while with the other, she manipulated my balls. Then she pushed her face into my ass crack and her tongue invaded my hole.
It wasn’t my first rear invasion as I had inserted vibrators and such there when she was on business trips, but it was the first time she had attacked me from the back. It was better than anything I had fuck myself with before. I started spurting and spurting and spurting. Harder and more than I ever remember.
My ankles wobbled and my knees gave way. I fell to the floor on to my own pool of cum.
During the next couple of days of practice, my strides around the apartment became more confident. “We need to test you outside.”
“What? You mean walk outside with high heels?” I asked aghast. “People might see.”
“Outside isn’t like inside. It’s bumpy and uneven. I want to make sure you don’t hurt yourself.” Cheryl tried to placate my hesitance. “As for being seen, it’s okay. We’ll tell them it is for the walk. I’m sure they’ll understand. It’s not like people won’t see you at the parade.”
Reluctantly, I started to get dressed. I grabbed a pair of Joe Boxer briefs. Okay they weren’t in the best of shape and were a little dingy and discoloured, but who the hell would know other than Cheryl?
“Eeew…! Is that all you have? You can’t wear those!” Cheryl said in a disgusted tone. She threw me one of her string thongs. I looked at her in shock and awe. “Think of them as a jock strap! Put..it..on!”
After figuring out what was front, I slipped one foot through then the other and pulled them up. The dental floss string was tight between my ass cheeks and got me excited. The small triangle crotch patch would easily cover my cock except I had an erection. The tip of my boner was sticking out the top.
Cheryl beckoned me to her and then pulled the thong down enough to expose my stiffy. I thought she was going to jerk me off or suck it. Instead, she made a circle with her middle finger against her thumb then gave my knob a hard flick.
“Fuck! That hurt!” I let out a high pitched scream.
“Oh, don’t be a girl!” She laughed. “Look. It’s shrunk to nothing now.”
Indeed my stiff was gone and was easily tucked inside the thong.
I finished dressing and outside we went. Other than a few cars passing by and ignoring us, we didn’t come across any friends or neighbours during my practice.
The evening before the walk while I was preparing dinner (in my heels and stocking of course), Cheryl entered the kitchen with a Chester Cat smile. She held a large paper bag up towards me. The bag was generic brown, I couldn’t tell what store it came from. “You’ve been such a good student. I have a prezzie for you.”
Excited, I put down my knife and reached for it only for her to pull it away. “Tsk! After dinner.”
The buttery Chardonnay went perfect with the scampi and wild rice I prepared. While I was excited and nervous and couldn’t eat, Cheryl ate and drank painfully slow. Dessert was French vanilla mouse which Cheryl enjoyed at the same slow pace. She would take a tiny spoonful and lick it off as if she was licking a cock.
Finally she was done. I cleared the plates and removed my long French waiter’s apron. Beneath I was wearing my stockings, garters, the thong panties and of course my fabulous high heel shoes. My top had gotten wet so I changed it to a white, tight sleeveless mid-cropped tee Cheryl had been making me buy and wear for practices.
We moved to the living room. She made me pour out a couple of snifters of XO as she took a seat in the big black leather chair. She sipped hers while I took a big gulp of mine. “So? What did you get me? Can I see? Can I see? Please?”
Cheryl handed me the bag. I cautiously peeked inside to see everything wrapped in white tissue before I reached in to pull out the first item. I unraveled the wrap and held a new package of stockings. According to the picture, they were black, RHT, Cervin Liberation 45 denier, semi-opaque, nylon stockings with four inch welts and black seam running up the backs of the legs. I looked at Cheryl.
“Well, I thought you should have something new and sexy for your debut!” Cheryl took another sip from her crystal glass. “Something of your own.”
The next package I unwrapped was a black, plain nylon garter belt with two one-inch thick straps dangling from each side. And finally, a pair of new nylon, teeny bikini panties. “Oh thank you, Cheryl. What a wonderful, beautiful gift. Can I try them on?”
“No, they are for tomorrow and I don’t want you to ruin them.”
Cheryl told me to follow her to our bedroom with the bottle of cognac. I was about to strip off my shirt but Cheryl told me to keep it on ’cause it looked sexy like I was wearing a camisole. She stripped off her outer clothes but kept her underthings on. The red bra, panties and garters got me hard in no time.
She laid back on the bed with her legs spread. I immediately attacked her vee with my face. The red satin panties were already stained dark with her pussy juice. I pulled the crotch part aside slightly to access her hole with my lengthy tongue. I lapped up the outpouring of juices as she came multiple times and begged me to stop.
We exchanged places. From between my thighs, Cheryl pulled my thong down over my boner. She carefully sucked it stopping numerous times to prevent me from cumming too quickly after each time I spasmed.
Cheryl hooked her palms on the backs of my knees and pushed my legs towards my head so I was staring at my pretty, red shoes. Being bent in half like that made my hard-on retract inside of me so only a couple of inches were evident. With my legs spread, my ass was readily accessible. Cheryl unceremoniously plunged her pointed tongue into my hole or rimmed it relentlessly.
I wanted to cum.
“Cheryl! Fuck me!” I begged. “Please fuck me! Fuck my ass!”
Cheryl understood what I wanted but had no idea how until I pointed to my bedside drawer. She opened it up to find a number of vibrators and dildos. She looked at me. “What the…?”
Cheryl quickly recovered and selected a toy. One of my favourites (well, okay they are all my favourites)! A stainless steel, round tipped tube vibrator; about five inches long and an inch in diameter. While I was still bent in half, she spat on my hole before she pushed it into me. When she pushed the on-button, I told her to push it again. It had a random pattern and power option.
Seemed Cheryl wanted me to suffer some and fuck my ass with the vibrator on the first setting. “Oh fuck! Oh fuck! God, please fuck me!”
I was on edge but just couldn’t cum. Then with only a couple of inches of it inside me, Cheryl pushed the random option button. The patterns went from pulse to scaling to wave while the power climbed from 1 to 10! Still I couldn’t cum. I squeezed my eyes shut hoping for release as I felt Cheryl push more and more of it inside me until I felt the tip of her finger against my asshole. My entire bowel started to vibrate. I felt the surge of cum rush from my testicles. I knew I would soon explode.
It was then I realized my pee hole was pointed directly at my face. Too late to react, the first blast of cream shot from my cock and splattered my face. With the vibrator selecting maximum pulsing power and inside of me, there was no stopping. Two, three, four powerful eruptions spewed over my face; in my eyes; up my nose; in my mouth.
I was shooting air when Cheryl finally released her finger hold against my hole. Still vibrating, the toy slowly emerged enough to be spat out by my asshole.
Cheryl released my leg hold and allowed me to relax on the bed. She crawled up and started to lick my cum from my face. She planted her lips against mine and kissed me hard. She used her tongue to force my mouth open. The cum she had licked up poured into my own mouth. With our lips still pressed together, I couldn’t spit it out and had to swallow my own cum!