Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between men and women. If this type of content offends you or you are under the age of 18 do not read it.
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Copyright 2011 Feb, All Rights Reserved.
Shelley begins to learn her place as a sissy
MM, MF, bi, anal, cd, toys, femdom *****
Karin and I had been happily married for about 10 years and had known each other through college. We were really best friends, still deeply in love, and enjoyed each other a ton. We had a similar sense humor, liked to travel, enjoyed our family, and had compatible hobbies that meshed in both time and interest.
Our sex life was good but not outstanding. Karin came most the time when we made love -- generally about weekly. She liked to have her pussy licked and I liked to lick it. Beyond this, things were fairly boring. It was always me pushing for new experiences and I didn't think Karin was really that interested.
I was about to learn there was a lot about Karin that I didn't know.
After spending the day a Jenny's, my plan was to come back through the garage, remove my bra, and then get into the house unnoticed, go right to the bathroom, and use my wife's nail polish remover to finish the clean-up and remove the remaining signs of my day out of the house. The pretty red nail polish on my fingers and toes was bound to cause lots of questions.
There was no problem coming into the garage and I replaced the silky lacy bra and white t-shirt with sports shirt I had in the car. I was still oozing Tom's cum into my panties -- wow does he cum a lot -- and was worried you could see a wet spot on my butt. I wasn't sure where Karin would be and was worried that the wet spot could give me away as I was trying to hide my fingernails.
As I came into the house Karin was in the worst place possible: the computer right in front of the bathroom.
"Michael is that you?" she called from the landing.
"Hey Hun. I'm home" I called back.
"I think we both had an interesting day. Why don't you come up so we can talk."
Oh shit, so much for trying to "sneak" in and be nondescript. I started to go up the stairs with my hands cupped so she couldn't see my fingernails.
As I got to the top of the stairs Karin asked "Did you like the taste?"
Almost instinctively I asked "The taste of what"? As I asked the question I could see the computer monitor and there was a picture of me on it. Actually it was Shelley wearing red panties, garter and stockings, my breasts thrust out, and my head tilted back with cum being poured into my mouth.
"Your cum. Jenny forwarded me some very nice pictures of your initiation. You show quite nicely." As she spoke I watched her scroll through picture after picture. My mouth wide open for Tom's spraying cum, my nose buried in Chuck's pubic hair with his cock buried deep in my mouth / throat. Tom fucking me from behind. The last one she looked at was my tongue arcing nicely into Tom's asshole.
"Oh my. Did you like eating his ass?"
All I could do was stare at the screen. I couldn't believe Karin was looking these pictures. I couldn't believe that Jenny had sent them to her. "How did you get these pictures?"
"No No. Shelley, I asked you if you liked shoving your tongue all the way up Tom's ass"?
"Yes." ....... "I loved being their slut today".
"Good girl. I was hoping you'd be telling me the truth tonight. Not that I didn't already know since Jenny and I have been planning this for a couple of months now. I have some things to tell you as well.
"I know you've complained for years that I didn't have the same level of interest in sex as you do. Today I learned that wasn't true. I just hadn't found what I wanted." With that she pushed the "next picture" button on the screen and my tongue in Tom's ass was replaced with a picture of my naked wife with a large black cock in her mouth and another in her pussy, followed by shot of a black cock in her ass and another in her pussy, followed by a huge puddle dripping from both.
"I'm not sure who had more fun, you or me. I do love big black cock and I loved having both of them in me at the same time. Especially when they came together. I could feel everything pulsing.
"Come here. I need some help which I think you'll like."
As I got closer to her, she opened her robe displaying her ruined pussy and cum still oozing out of her. "Could you clean me up? Feel free to suck my ass just like you did Tom's. Darrell left a bit of a mess."
I dropped to my knees. After just a couple of minutes working on her pussy she shifted me to the floor and lowered her ass to my mouth. "Suck you little slut" and I was given no choice on where to put my tongue. She was right. Darrell had left a bit of a mess.
Afterword, we got ready for bed and were cuddling next to each other.
"How did you do this?" I asked.
"Almost by accident. I had gone over to Jenny's when she was in the middle of a session with Chuck. He had lost a bet and was tied to a chair in her living room with a web cam focused on him.
"I'm not sure why she let me in but it was hard to miss the naked man tied to a chair with his cock as purple and hard as I could imagine one getting and she asked me `Would you like to make him cum?' Chuck definitely wanted to cum and was begging her for relief. I'm not sure what would have happened if I'd said no, but I was curious. I squeezed his balls and stroked him maybe twice and that was all it took. Apparently she had been teasing him all morning.
"This obviously took our friendship in a new direction and we spent a lot of time together discussing sex, what we liked, and what we wanted. Somewhere along the line I described your desires and fantasies and that opened a whole new door. What happened [she looked at the clock] yesterday was both the fulfillment of my plans for our sex life and the start of something new."
"What sort of something new do you have in mind?"
"Jenny and I are still working that out but we've confirmed your desire and willingness to be our little sissy. I've decided I really like having Rodney and Darrell around so you will be seeing more of them'. She smiled and almost laughed. "I expect all 8 and 10 inches of them as my little sissy as well".
"You should get some sleep. The kids are at camp for the next two weeks and Jenny will be calling you in the morning.
The phone rang at 7:30 in morning "Hello".
"Is Shelley home?"
It took me a minute to wake up, process the request, and realize it was Jenny.
"Yes Mistress."
"How did you like the pictures?"
"We liked them a lot. I think my wife has a favorite or two as well Mistress. I was quite surprised."
"I'll bet you were but it sounds like it was a good surprise. You are to be here by 8:30, very smooth and dressed exactly as you left last night." Click.
I quickly got up showered, shaved very smooth, and got dressed. Coming home last night there hadn't been anyone out or about and the visibility of my bra and thong wasn't a big deal. This morning was different matter. Of more concern was what would happen if I was punished again. The large plug hurt a lot. I could only imagine if I failed her two mornings in a row.
It was 8:25 when I was set to leave the house. Karin wanted kiss and pulled me close. I could feel her hand rubbing across my bra strap and the other sliding down my pants. In playfulness, I had often teased her by undoing her bra and she just returned the favor. She also pulled my thong all the way up -- which also made the top of the panties clearly visible above my pants. "You have fun now" was her offering as I looked and stepped out the front door.
There were three people on the way to Jenny's. Someone walking a dog that I'd never seen before; Chris, the neighbor from two doors down who was busy in her yard but did seem to look up as I crossed the street in front of her (I couldn't look back); and Mr. Johnson, Jenny's next neighbor. He definitely saw me coming. Glancing over as I turned on to Jenny's walk he was watching me the whole way.
I rang the door bell and Chuck answered, inviting me in. He was wearing running shorts and a very sweaty t-shirt. "You are supposed to be on your knees when servicing me" and he pulled his running shorts aside. I dropped to my knees and could see and smell the sweat from his run. "Go ahead. I know you love my cock in your mouth" and I began to lick his sweat covered balls.
"Shelley, we really have a lot to do today and you'll have plenty of opportunity to serve later. In the meantime you can stop sucking my husband without permission. Now come here, we have things to do."
"Yes Mistress" as I followed her back to the master bedroom and Chuck smiled at me on the way past.
Carefully laid out on her bed was a complete ensemble ... a wig, my breast forms, a yellow bra and matching panties, stay-up stockings, a pretty yellow dress, my slingback heels, and a small purse. "We are going to have fun today and treat ourselves to the salon and spa, and some shopping. I need you to hurry up and get dressed so we can be on-time for our appointment. I'll help with your wig and breasts and then I need you to get dressed on your own."
This time when she applied the forms she applied a cream to make sure my chest was absolutely smooth and it seemed like she put on more glue than last time. As if reading my mind "They're not coming off so easily this time." Once she'd attached and set the wig "Ok, it's all you" and proceed to get herself ready to go.
Once dressed, the outfit was quite pretty. I tried to tuck things into the panties to be as flat as possible but if you looked closely there was still something there. It also looked like I could have used a slip. In the mirror, you could see the bumps of my nipples and a faint coloring of the areolas, and if I stood in the light you could see right through my skirt -- which hit me just above knee. If I needed to bend over at all -- how does a lady do that? -- you'd be able to see the tops of my stockings as the dress rode up. All in all this was a look I loved to see as a guy and I expected I'd be getting more then a few interested looks today.
The trip to salon / spa was a bit of a whirlwind for me. Jenny had a bunch of things in mind for me at the salon. I was to get my ears and nose pierced, a facial and then complete make-up application, exfoliation (the were still some rogue hairs on my back and on other hard to shave places), a mani and a pedi, an enema to clean me out, and they'd be taping or glueing my "package" out of the way. She also told me I'd be paying for this visit for both of us and she'd put my credit card in my purse.
As we prepared to leave it was way more than I had expected. I had a new set of ear rings in my ears and a stud in my nose, my face was fully made-up, I had lovely nails that were way longer than I was used to, I was clean from the enema, and they'd pushed things around so I was almost totally flat and had a lovely labia with pretty folds and no manly bumps to give me away.
Jenny was also nicely made up but looked very relaxed as we walked to the counter. I handed my card to the cashier "Shelley you look very lovely. Make sure you take care of your new piercings and hopefully we'll see you again. We just love making you look pretty."
"Do you want to grab a bite to eat?" Jenny asked as we left the salon. "There is a nice little restaurant around the corner."
"Yes Mistress. That would be wonderful."
At lunch she explained what would be happening the rest of the day. "Tonight, we are going to have a party. I have several friends coming over including your wife and her date, or maybe dates. I'm not sure. I will have a special outfit for you but your job is to serve my guests however they please. My guests may ask you to do anything and I expect you to do it without question. You seem to enjoy being my sissy and I expect to able to count on you."
Lunch had been served and between bites she told me I needed to buy some clothes at the mall and then we needed to hurry home to prepare for the evening.
"To make things simpler, I've written down your sizes" she said as she passed a note across the table. Jenny was half laughing at me as I tried to figure out what to with it before settling on my purse. "You'll be staying with me until Monday and will need clothes and shoes to wear. I love your slingbacks by the way."
"Mistress, I really need to use the rest room."
"I can come with you if you'd like."
"Yes Mistress."
At this point I tried to follow her lead so I knew what to expect. It was my first time in the women's restroom as woman. Once in the stall, I carefully lifted my skirt and pulled down my panties. I thought about some of the outfits my wife wore and how she'd almost have strip naked just to go. It felt both funny and very feminine to have to sit to pee. There was no standing with things stuck down as they were.
Jenny was waiting for me in front of the mirror checking her make-up and applying fresh lipstick. She showed me what to look for just as two other ladies came in. I'm not sure whether I didn't quite pass or if the couldn't figure out what Jenny was doing but they definitely gave me / us a strange look. I applied my lipstick as Jenny'd shown me and we went back to our table.
"Thank you so much for lunch Shelley" Jenny offered as the waitress walked by and she came back with the bill.
The trip to the mall was going to be more of a power shopping spree. I could tell Jenny was in a hurry and that she had a general plan for what we'd be getting and the stores we'd be going to.
As we walked to the center of the mall and to our first store, Jenny was really cruising along and I was having a hard time keeping up. It was one thing to walk casually in heels and I'd practiced enough to be ok at that but we weren't walking casually.
"Jenny" was all I got out and then I was stumbling toward the floor. As is usually the case when you do something graceful, your first thought is "am I ok?" and your second is "did anybody see me do that"? I was pretty sure I was ok, but I fell right in front of a table of guys on the edge of the food court. Falling is never graceful but falling in a short skirt and cute stockings is something else and I was sure most of the table saw and were seeing everything up to my pretty yellow panties.
One of the men got up to lend a hand as Jenny came back to rescue me. "Can I help you up miss?" As offered me his hand, he pulled me up and close to him and I felt our bodies come together. I'm sure he felt my breasts against his chest and my hip against his thigh.
"Thank you."
"You are very welcome. You can fall in front me anytime."
Jenny moved to help me and asked if I was ok as she turned me away from him and lightly dusted me off. It took a second but she got me pointed in the right direction and we set off at a slightly slower pace. The Victoria's Secret store we were going to was almost right there and every guy at the table watched us walk in and I'm sure that sparked some conversation.
With Jenny's help we were able to make some quick selections on lingerie and I went to the counter with a couple of bras and panties, a garter belt and a couple pairs of stockings, a pair of knee socks, a camisole, a corset, and a very cute babydoll nighty with matching panties. As she rang everything up I realized just how expensive lingerie really is and handed her my card.
"Michael can I see your ID please?" she asked as I looked her almost panicking.
"Yes Michael, show her your ID" Jenny offered.
I handed her my ID having no idea if that would help at all. "Is this your brothers or something? We may need to call the police about this."
"Can I speak to the manager? I can explain."
"What could you possibly have to explain? You stole your brother's ID and you're trying to use it to buy $380 worth of our clothes. I'll call my manager but she's probably going to call security. You stay right there." She picked up the phone and had a quick conversation. "She'll be right here."
A few minute later a woman approached "I'm Maureen, the store manager, you'd like to talk to me?"
"Uhhh, yes. I was trying to buy lingerie but wasn't able to check out."
"I know that. You're trying to use somebody else's card. Do you know you can get into a lot of trouble for that?"
"But it is my card."
"Steph. Do you have her credit card and ID?"
Steph walked over "Here you go Maureen" and gave me a "yeah right" look.
"Michael appears to be male on this driver's license. How would this be yours?"
"Because I'm a he. I can show you" I almost whispered. You could see the look of amusement on Maureen's face as she thought through this. "Could we use your dressing room? Please?"
"I think I'd like to see that."
Once in the dressing room I lifted my skirt and pulled out my panties. "See."
"Um no. I was expecting to see a little more .... cock here."
I pulled my panties all the down way and lifted my foot on to the chair to give her the full view of everything tucked and taped away.
You could see the edge disappear from Maureen's face "Honestly this isn't something we see everyday. You know this is why they have the internet right?"
"My Mistress suggested we shop here instead. May I get my things?"
"You are very nicely made up. I'll have Steph check you out. What is your name?"
"Shelley."
"I'm sorry Shelley. We have a lot of problems with bad credit cards so I've told my girls to pay close attention. I'll wait for you outside as you get dressed."
It didn't take long to adjust my panties and straighten my dress. As we walked to the counter Maureen said, "Steph, can you check Shelley out for me please? Here is her card and ID." Turning to me, "And here is my card. If you'd like to shop with us again please ask for me and I'll take special care of you."
Maureen saw Jenny had been standing off to the side as I finished checking out. "Is this your mistress?"
"Yes Maureen. This is my Mistress."
"Hi Maureen. I'm Jenny. Thank you for all of your help today. Shelley, are you ready to go now?"
"Yes Mistress" I replied as we started back into the mall. The guys were still sitting at the table across the way. I knew they didn't know what had happened in the store but I was sure I was still blushing as I watched them watch me.
It took two more stops to get the rest of what I needed in two blouses, two skirts, and a pair of mary jane shoes. I'd asked Jenny if she could buy for me and I'd pay her back so we wouldn't experience the card fiasco again and the guy in the shoe store was trying to get a good look up my skirt as I tried on shoes but I think I did a good job of keeping my knees together. With that we were off to the car and Jenny said she had one more stop to make.
We passed a sign that said "Ye Olde Sex Shoppe" that advertised "Adult Novelties" over a picture of two busty female silhouettes sitting back to back with "Live Girls" and "Adult Shows" on the marquee below and Jenny slowed down and pulled into the lot.
"Shelley, this is our last stop. We have a party package to pick-up for tonight and we should be all set. In addition to the surprise in the package I'd like to pick out a nice dong to model. I'd like it to be large; perhaps not as thick as Tom but definitely longer."
There was a security system where you had to show your ID to the attendant to get into the store. The guy -- who looked every bit like the stereotypical dirty old man -- took our ID's and gave us the once over.
"Welcome Miss Jenny, good to see you again. I see you brought a friend with you."
"This is my sissy Shelley. We've got to get her ready for a party tonight and I'd asked Jeff to help us out. Isn't that right Shelley?"
"Yes Mistress Jenny."
"Shelley looks like quite the hottie" he said as he handed back our ID's. "I bet she loves to fuck."
"Earl, I bet you're right" Mistress' replied as the door opened and we passed through to the inside of the store. I just followed meekly behind Jenny.
"Hi Jeff. How are you?"
"Jenny, it is great to see you" and they hugged briefly.
"We're having a party tonight and I think you have a package put together. Can I pick it up? Jenny why don't you go take a look at the selection."
"Yes Mistress" as I excused myself looking around at the various sections they had to choose from. "Lingerie", "Novelties", "DVD's", "Adult Games", and "Live Shows" were the choices and I opted for "Novelties" section. It was amazing what you could find. There were plugs, vibrators, & dildos in all shapes and sizes. There as a rubber fist about the size of my arm. I'm wasn't sure what you could do with that. Settling in the corner was a range of dongs. There were a couple that caught my I eye but the one I liked most was 10 inches long and about an inch and half wide with a sexy mushroom head, veins, and flexible balls. I was a lot like the one I had at home but black.
As I went to show Mistress Jenny and she walked to the counter and Jeff.
"Shelley, the cost of the party package plus the dong is $375 and we'll throw in some free lube and cleaner." I opened my purse to give him my card and he said "I'm sorry, we don't take Visa, but I'll tell you what. Jenny has offered you to model this for us so we could probably work out some type of a deal."
"How would I model it?" I asked.
"Well, we have a live show starting in 15 minutes and we'd like you to do it then."
"Jeff, Shelley would love to do it. Which room would you like her in?"
"How about door #3?" and Jeff pointed at the door to his left. "I need to open and clean this to get it ready, but I'll get it to you in a minute. Go ahead and check out the room to get comfortable."
Get comfortable? I was scared shitless. In the room was a padded table about 4 feet high and three feet wide. There was a little bubble in the front corner for a camera, a mirror on the back wall, and the drapes were closed. This modeling thing could hurt. Tom had opened me up yesterday and the enema had cleaned me out, but this was still a big dong.
A few minutes later there was a knock at the door and a girl with a cat shaped mask, whiskers, a see through top, and almost non-existant skirt came in holding the dong with a bottle of lube.
"Hi Shelley, I'm Desiree. We've got about 5 minutes to show time and we need to get you ready. I'd take off the skirt but you can leave the panties on -- personally I think it's hotter that way." Once I'd removed the skirt, she said "Ok, go ahead and bend over the table and spread you legs outside of the pads on the legs. There is a spot to put your hands up here." Once I'd assumed the position, she said "Now I need to attach the restraints." I wanted to say "No" but wasn't close to fast enough. She had the ones for my hands attached first and they were soft to the feel but I was pretty sure I wasn't going anywhere. Then she did my legs and I knew I wasn't going anywhere. She grabbed the tube of lube and basically squirted inside of me.
A moment later the curtains opened and the music started. Looking up in the mirror I couldn't see how many people were in the audience but I could here them and it sounded like a lot.
Desiree did a dance that included wiggling her cute little ass about -- she had no panties on -- grabbing and fingering me, and prancing about with dong in her hands intimating where it was going to go. The crowd got louder and she finally pushed the head of the dong into me. Then she pivoted the table and me 90 degrees and finished by thrusting her hips against the dong to push it all the way in to me giving the appearance of my getting a good fucking. The crowd went wild and the curtain closed.
"You were wonderful" she said.
"Wonderful? You did an amazing dance. I was just strapped to the table."
"True, but you took it so well.
There was a knock on the door and Jenny and Earl came in and Desiree stepped out.
"You modeled that very well Shelley. How did you like it?"
"Mistress Jenny, I've never had that large an audience before but they seemed to enjoy it."
"Indeed they did. Damn near a sellout crowd. We made a fortune on that one."
"Shelley. We have one more little thing to do here before we can go. Earl wants a piece of your pretty little ass."
"Yes Mistress."
Earl was standing behind me and pulled the dong from my behind. Then he grabbed my panties with a tug and ripped them off. The next thing I felt was Earl entering me and him sliding in and out. It didn't take long before I felt Earl tense up and his cum squirting inside of me.
As he pulled out he said "She's not very tight".
"No Earl, it's just that you have a little dick. You've had your fun now run along."
Earl left as Jenny released me "I am sorry Shelley. That wasn't part of the plan. I promise you'll tonight's party will be better and more fun. You're a great little sissy."
"Thank you Mistress. Why did this happen?"
"Chuck lost a bet to Earl and you were the prize."
I hope you this was a big a thrill to read as it was to write. Feedback appreciated on both style and substance.