Lou Ciphers Tale

Jane worked for a company on the floor above mine. I was a marketing rep and she held a similar position at her company but she was involved in the medical field I dealt with pretty boring consumer products. We had met on the elevator a few times before we finally went for lunch together and then on a few dates.

We were both single. Well she was widowed and I was divorced. A result of my philandering ways. It cost me plenty but I had moved past it and I believed my ex, Sharon, had also, as we were still friendly though saw each other rarely.

Jane, like me, was her early 40's and we seemed to click on many levels. We enjoy the theater, dancing, rock and roll music, dining out and hot sex. We loved trying new things in the bedroom and would often tie and tease each other until the wee hours of the morning.

I still dated a couple of others and thought that she was doing the same. I mean we never discussed being exclusive so why not. It would not have bothered me if she did. I guess men and women just don't think the same way about those things.

Halloween was coming and I agreed to go with Jane to her friends party. She said she had our costumes picked out and although she would not let me know what they were I was to take the day off from work and be at her house at noon to start preparing. Always up for a fun party I had no problem with that. I knew she would come up with something fun for us.

Jane was a statuesque red haired beauty. At 5'10 with long hair and a great gym fit body was the envy of most men and women that gazed upon her. I was only 5'7' with a decent build but could afford to drop a few pounds. I was a good looking guy but most women considered me "cute" as opposed to handsome. I more than made up for what I lacked in the manly looks dept. by my great personality and wit. As a holdover from my days in a rock band years before I still had my shoulder length hair and and was a fairly accomplished musician.

I arrived at Jane's' on Halloween day as expected finding her in a silky sheer nightgown with a tiny g-string panty underneath. She handed me a robe and told me to strip and put it on, which I wasted no time doing as my 7 inches hardened at the sight of her. She lit a nice joint rolled from her medical pot and we had a glass of wine. She told me we were going to shower together before continuing our day.

Pleasantly stoned I followed her to her bedroom where I took off my robe and we embraced for a deep kiss. She then disrobed as I gazed upon her beauty. Pointing to my hard cock she told me to forget it as there would be plenty of time to use it later. She handed me a blindfold saying she wanted me to just feel the pleasure as we showered. She led me into the bathroom and helped me into the tub.

I was still excited thinking about how hot and kinky this day was starting and how great it promised to be. She told me to put my hands up over my head and before I knew it she had them secure in handcuffs she had placed around the shower head. No wonder she wanted be blindfolded. The water was freezing at first when she turned it on causing a yelp from me and my cock to shrink before it started to warm up a couple minutes later.

The water went off and I felt fer hands caressing me. Spreading shower gel all over me from chest to toe. Lovingly spreading it around my chest and crotch. Bringing my cock hard once again. With a hard slap to my ass she reminded me I didn't have her permission to get hard again.

"Don't go anywhere darling, I will be right back."

"Yes my lady."

I waited and waited and started to feel a burning tingle all over my body. Jane finally returned and put the joint to my lips and with a laugh, told me to suck. I took a deep hit and she unbuckled the blindfold and turned on the water. As I exhaled I watched what little body hair I had wash down the drain as Jane stepped in and unlocked my handcuffs. We slowly washed each other and I made my way to my knees and licked her beautiful cunt and clit until she could no longer hold back and her delicious juices filled my mouth.

"OK my smooth lover time to dry off."

We dried each other in fluffy pink towels and went back to the bedroom.

"So what are the costumes for tonight honey, you haven't told me yet."

Pulling some items from her closet she said, "jeans and leather shirt, some leather chaps and these boots, I am going as a biker."

"Wow that looks pretty hard core. And what about me?"

"You dear are going to be my biker chick, my hot wife. A loving slut to your hot biker dude. And you are going to do a great job of it without complaint. Wanna know why? Of course you do. Because when its done you are gonna have such incredibly hot sex. Such unbelievably amazing sex. It will be like the worlds gonna end tomorrow and its the last sex you will ever have and it will be so fucking awesome you will never forget it. That's why!"

"Wow you really seemed to have put a lot of energy into this. How can I refuse an offer like that? So where's my outfit?"

"You don't get to see it yet. Get dressed in your clothes we gotta go out for a bit to do some prep work. When we get back I will dress you."

After dressing she led us to her car and we soon pulled into a small strip center not far from her home. We got out and she led me into her regular beauty salon Curl Up & Dye. Upon entering I saw it was quite busy being Halloween. All the stylists were in costume. Kittens, Lions, an Oktoberfest waitress, Freddy. Jane was greeted and led to a hair stylists chair. I was led to the nail area.

For the next 2 hours I was pampered and prettified. After a wonderful pedicure and foot massage my toe nails were a deep bright red My fingers were next and as they were started Jane came back over. She was still wearing the tunic top and leggings she had worn here but now her long red hair looked a greasy mess of red and black. Her face sported a professionally applied mustache and shaggy beard. Her brows were bushy and over grown.

"What do you think Phil?"

I was shocked but told her it was amazing but wasn't it a bit much for a party at a friends house. As she was explaining that it was also a charity fundraiser and had a $1000.00 prize and special gift for the winners, I noticed the nail tech adding length to my nails.

"What are you doing to my nails? That looks really long?"

Mi-Lin, the nail tech said they were acrylic extensions. She said she would cut them down before finishing them off. Jane told her that 1/2" would be fine. Mi-Lin soon finished and my now very long very strong nails matched my red toes. Except my ring fingers that had a sparkle coat added to them. She said it was called party nails.

I was taken to the shampoo area and my hair was washed as I looked at my nails with some concern. When I was soon seated in my stylists chair the lady next to me said. ""Wow you are very brave to get nails like that. Those acrylics last for weeks."

I called out for Jane but was told she went next door to the convenience store to get some snacks. The chair was tilted back and the stylist started combing and cutting my brows shorter with a tiny brush and scissor. She soon applied some warm wax and pressed a strip of cloth down on it. Ripping it free it felt like my brows were totally torn away. She reassured me they weren't and did the other eye. I was told how much better they looked and reminded they would grow back soon.

I didn't realize how much Jane wanted to win this contest and decided that the promise of that nights sex would be worth it to just go along with it without complaint.

I was turned away from the mirror and saw Jane return. As my hairstyle was beginning to take shape she handed me a drink and said how hot my nails and brows were. She couldn't wait for me to be finished. I did ask about the permanency of the nails and she just said I could cut them off when we were done.

As my stylist finished and turned me to the mirror I was shocked to see my shoulder length hair was now cut in a very feminine bob. Not really long enough to pull back into a ponytail as I preferred and no way to hide the very sexy lady's style. I was disappointed by knowing I would have to cut my hair off before going back to work.

"With that look I think you will now be called Felicia. We can't really call you Phil anymore can we?"

So with my feminized face and men's clothes, and Jane in her feminine clothes and bearded face we headed back to Jane's place. Into her bedroom we went and our clothes were quickly off as she directed my mouth to her pussy. She was so hot and moist I felt like I was in heaven as I licked and caressed her clit and brought her off multiple times. She only yelled at me twice for poking her with my now much longer nails. She finally had enough and we quickly went and rinsed off in the shower.

She pulled a box from the closet saying it was time for me to dress. She handed me something called a gaff and told me to put it on and it would hold me smooth. I was too stiff to tuck myself in the way she said and she came over to help me out.

She held my dick and told me to look up. As I did she took the flat side of her hairbrush and smacked it down on my cock. 3 hard strikes and I was howling in pain. But it did the job and she got me tucked tight, telling me to be a good little slut and behave. Next was a black panty girdle with red trim and 6 garters hanging down from it. This was even tighter than the gaff and now I looked as smooth as any natural female.

"Isn't this a bit much? After-all I will have a skirt on too ya know."

She started rubbing my smooth crotch making me breath hard as she whispered softly in my ear. "You are my little biker bitch tonight, Felicia, and you will do what you are told or be treated like one starting now. I suggest you save your energy for the party."

"Yes Miss Jane."

And I think you better start calling me Lou. That way you will have enough practice not to make a mistake later.

"Yes I like that Lou's Bitch. Lol."

Fishnet stockings were next and they were attached by 3 garters each. I realized going to the bathroom later would be difficult. Lou then produced a black and red corset that matched the panty girdle. She fitted it around me and laced it up so I thought I wouldn't be able to breath. I was instructed to take small breaths into the top of my chest and I would be OK. The bit of flab I did have on my front pushed up and completely filled the B-cup bra built into the corset. I would have plenty of cleavage to show of tonight it appeared.

A short denim skirt was buttoned around my waist. Little bits of fringe tickled my legs. Some tacky rings and necklaces, some bangles on my wrists and huge hoop earrings were next. Then came the shoes. Fuck me red pumps with a 4 inch heel. She slid them on my feet and wrapped the ankle straps around and buckled them. Then Lou pulled out a couple of padlocks and locked them on.

"You better get up and start practicing your slut walk now bitch."

Lou pulled out another joint. Saying she would do my makeup after she dressed she started to dress herself. I saw her pulling straps up her legs and then fit a realistic looking dildo into it. One end was gently placed to give her the most enjoyment and then the 8 inch cock hung out like the real thing. She pulled on a pair of boxers before a pair of men's jeans and biker boots. Next she used a sports wrap to compress her breasts as much as possible as she has a beautiful C-cup chest.

Over this went a men's denim styled leather shirt and a leather vest. I was so hot from watching her as I stumbled around trying to learn to walk again. There was no way I could get hard trussed the way I was. Dammit!

She finally had me sit and started on my make up. When I was done I had waterproof mascara (she said she didn't want it to run later), Blue eye shadow and dark liner extending well past my eyes. My lips matched my nails and she said the lipstick was good for 24 hours.

I looked in the mirror and saw a total slut looking back. The typical television biker bitch and next to me was my biker dude Lou. Someone would have to go a long way to beat us tonight.

We had some light snacks as there would be plenty of food at the party. It was nearing go time and I must say I was a bit nervous going out looking like this. At least she didn't have a Harley.

I put the snacks away in the Kitchen and went to the living room to get the small purse she prepared me and saw Lou sitting in a straight back chair.

"Come here Felicia."

"Yes Lou."

Catching me off guard he pulled me over his lap and with hardly any protection on my end he started spanking me with a small wooden paddle. I was kicking my feet and crying hardly able to breath in the corset.

"That's to make sure you understand you are my bitch tonight and will do everything I say with out thinking. Got It?"

"Yes Master Lou."

I patted my tears dry and Lou said there was one more thing to do before we left.. He turned me around and tightened my corset even more, admiring how she thought it made me look sluttier. As if that was possible.

We headed off to her friends party. It was in a mini mansion in a gated community. Being close to 9 there weren't many trick or treaters still around but there were many cars parked around the her friends home. A large sign out front welcomed guests to the charity ball. We were greeted warmly at the door by a French maid and a butler. It was Jane's friend Carol as the maid and her hubby Ron as the butler. We were given little # tags to put on for the costume voting later.

I finally found out the charity was for the local women's shelter and there was a table with gifts for a silent auction fundraiser. Jane, rather Lou, told me she had already sent over a piece of artwork for the event.

The costumes were awesome. With many of your usual Dracula and Wonder Women outfits, French maids and pirates. Even 3 other guys dressed as bikers but none as good as Lou. Saloon girls and beer maidens and cowboys. Knights of the realm and a princess. Looked like I was the only slutty biker chick.

As I went to get us drinks from the bar I noticed Lou talking with an apparent Leather Mistress with a Zorro type mask on . As I approached them with our drinks I could see she had a really hot body accentuated by a leather corset and hot-pants over legs that seemed to go on for miles. A crop and paddle hanging from her belt and hand cuffs on the other side. Totally hot if you are into that kinda thing. And Lou and I certainly were.

"Kneel here and wait to serve me my drink bitch."

She pointed to her feet and as I knelt she pulled the other woman to her and kissed her deeply. Her tongue invading the Mistresses mouth. I moaned as I felt the pain of not being able to get hard in my girdle and gaff and watched. The Mistress she was kissing seemed a little familiar, but I could not place her. When they finally separated I handed Lou her drink as she introduced me to her dear friend Mistress Helga

Yes, she did look familiar but her German accent told me I was wrong. I guess I just wish I knew her. Lol.

The evening was going smoothly with drinks and vapes being enjoyed by all. The auction results were announced and then the costume contest. Lou and I were called to the front of the room with 2 other finalists. Wonder Woman was one and the saloon girl in a gorgeous purple satin period dress was the other.

The Maid/Hostess was Master of Ceremonies and was assisted by her hubby/butler. He held his hand over each contestant looking for applause. Our applause was the highest and Lou was presented with the winner check and a small package. Lou immediately donated the winners check back to the charity and we went back into the group to much applause.

Many were shocked to find out that Lou, with the large bulge in his pants was actually Jane and that I was a male.

After a few more drinks and some finger food Lou pulled me to a quiet corner.

"Okay Felicia, you have been wonderful so far tonight. Let us hope it continues. Remember I told you that you would have the best orgasm of your life tonight? Well it's almost time to make that happen. You are going to cum like never before and possibly like never again!"

That had an ominous ring to it but I was too horny to care. I just wanted to get my cock out of these pantys and into Jane. She said we were going to a pvt room upstairs that had been set aside for us. I was told to grab us each an extra drink and meet her by the stairs. When I got there she was waiting with Mistress Helga, the 3 biker guys and Alice in Wonderland.

"Where are we going Sir Lou?"

"Its Halloween bitch! You are going to Hell!"

They all laughed at that and hustled me up the stairs to a room at the back of the home. As we entered it appeared to be a hidden home dungeon. Chains and whips on the walls and orange candle all around. Fake bats hanging from the ceiling and cobwebs in the corners. Comfy chairs surrounded a large padded bench and a cot. Straps attached to both in all manners. I took in as much as I could before Lou spoke softly to me.

"You pleased me tonight my sissy bitch and now you get your reward. You will be rewarded with your orgasm soon but first you will be Lou's toy and put on a private show for our little group. Be careful though you may never want to be Phil again when we finish."

As she said that a cloth was placed over my mouth and nose. I couldn't tell what it was and tried to struggle away when I realized that 2 of the biker dudes were holding me tight. I could do nothing but inhale the fumes. I felt weaker and hornier with every breath I took. How could that be? What is that stuff?

"Yes my slut enjoy sniffing that sissy sauce. Take it deep and be my helpless sissy now."

I felt my clothing being removed. My skirt dropped to the floor and my shoes were unlocked and removed. My garters were unclasped and the panty girdle and gaff came off. In just the corset I was bent over the bench and quickly attached. My legs spread wide and strapped down. My wrists were next and a wide strap over my corseted torso held me firmly.

The prize box was opened and a a metal ring and disc were removed. The metal ring was soon slipped over my cock and balls causing my cock to harden. Lou stood in front of me and showed off a wooden paddle with holes drilled through it. She smiled devilishly as she swung it effortlessly through the air against her palm as if testing it. A blindfold was soon over my eyes leaving me in the darkness.

"Well Felicia, part of the prize at this party is to take a bit of revenge for all the women the shelter benefits and you as this years winner get to enjoy it all. Now breathe deeply cause this is going to hurt a bit as we turn that sissy ass dark red."

The cloth was held to my nose again and I felt the first whack of the paddle on my ass. I cried out in pain but couldn't stop the blows. Everyone in the room had a turn with the paddle and Mistress Helga was the harshest of all of them, totally blistering every spot of my ass. The poppers weakened me to a soft whimper as each stroke fell. The cloth was removed and as I gasped for air I felt something at my lips. I figured it was Lou's dildo and I heard her voice.

"Suck it like a good little bitch Felicia. I know you want to earn that big "O" I promised you."

My cock was like a rock with the metal ring over it and even with my ass a blistered red I was as horny as I had ever felt. I opened my mouth and sucked in the phallic object and felt it harden in my mouth. As the blindfold was removed I saw it was a real cock. I wanted them to stop but could not talk with my mouth so full. Another entered my burning ass and I realized it was the bikers cocks not Lou's dildo and I was being helplessly raped at each end.

"Mistress Helga would you please work over her sissy cock while she is fucked. It makes me so hot to watch you play."