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.
Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at your own site, please contact the author for permission.
Copyright March 2011, All Rights Reserved.
Jenny describes Michael's transformation from Michael to Shelley
MF, MM, bi, cd, toys
Introduction
Hi, I'm Jenny.
I hope you are enjoying the Shelley's introduction and thought you'd appreciate knowing the other side of the story and how we got to this point.
First, I'm as Michael described me. I'm a well put together redhead. What you didn't get from Michael, but may have picked up along the way is that I really like sex and it is a big part of my life. I enjoy being an active hot wife and am definitely the dominant partner in the relationship with my husband and others. Oral sex is a lot of fun -- both giving and getting -- and I love to swallow. Why waste a good thing. High on my list of things to enjoy is being filled with cum and having my husband or lover lick me clean.
Being very sexual in a small town does create some issues with visibility. It's very easy to have people know a lot more about your preferences and lifestyles than you may be comfortable with -- and you never know where those meetings will occur. We've tried to simplify this by having a discrete group of folks that know about our lifestyle but it is a challenge. What started as an interesting conversation resulted in a new lifestyle for Karin and Michael ...... *** "I'm wondering if Michael is gay?" Karin asked on one her frequent visits. "Excuse me. Your Michael?" The same Michael that I catch looking at my boobs? I want to snap my fingers and say "Hey, my eyes are up here'"?
"Well yeah. I know he likes women but there are just a lot of strange things going on with him." "Like what?" "Well he's just been getting a lot more feminine lately and then there are the toys." "Toys?" I asked. "Yeah ... well, let me start from the beginning. Michael has always been very interested in sex and trying to convince me to try new things. Normally I humor him some but it takes me a while to accept and try new things." "Like what?" "Like eating me after we make love or kissing me after he's gone done on me." "Do you think that's gross?" I asked at the same time thinking that I couldn't wait to have someone suck my cum filled pussy. I loved having Chuck eat me after someone had filled me with a huge creampie.
"Yeah kind of. I don't like the taste of me and I can't figure out why he likes the taste of him, but that's not the part the really concerns me. It's the lingerie. He's been wearing panties and other clothes and shaving his legs and other body hair. It's just freaky. Normally I don't share this kind of stuff but I need to tell someone." "He's wearing panties? What does he say about that?" "He says he likes wearing women's clothes and likes it when the woman takes charge." "Does he want you to take charge?" 'Yes and when I asked him about that it gets even weirder. I asked him what he'd to and how far he'd go as a woman. Would we suck cock? Yes. Would he let a man do him? Yes ...if I made him do it." "So you're thinking that he's dressing like a woman and the rest and he must be gay?" "I don't know, but it just doesn't seem normal." "You're married to him and probably know him better than I do but I really don't think Michael is gay. He may have some ...... interesting sexual desires but nothing I see in him says 'I'm leaving my wife for a guy'. I also wonder if maybe there isn't more for you to explore here. Have you heard of the terms hot wife or cuckold?" "I've never heard of a hot wife, but I think I know what a cuckold is." "Well, a hot wife is a wife who takes other lovers with their husband's approval. Here, I'll give you a couple of websites that'll show you a bit more about the hot wife lifestyle" she said as she wrote down the URL. "See what you think of this and maybe ask Michael what he thinks of the idea." "I'm not sure I'm ready to embrace his 'interesting sexual desires' just yet but I will look at it."
*** A few days later Karin was over again. "I couldn't believe it. I checked out the hot wife blog site you told me about and was amazed at how many women love fucking strange men while their husbands watch or participate. I also loved the pictures stories of the wives getting pleased by huge black cock. I was totally creaming." "I told you it was pretty hot and that perhaps there was more to Michael then you were thinking." "Well, he's never really suggested that idea before. So far it's just been him and his panties." "Did you look at the cuckold sites I gave you?" "Yes I did. Those weren't as interesting to me but I did see some resemblance to Michael's fantasies." "I don't think we are all alike in what turns us on. We use lots of labels for things but really, try searching the internet for crazy sex things. Lookup guys having sex with goats on fire, and you need to qualify what kind of goat. From what you've said, Michael likes dressing up in women's clothes, wants to be dominated by the woman in his life, and will do anything she wants him too. This could be all good for you." "Except, I'm not a hotwife and I don't know what to tell him to do." "Yeah, but would you like to be? Don't answer now. Just think about it." Karin just looked at me and then we started trying to decide where we would both like to go for Spring Break. *** It turned out that Karin and Michael decided on a cruise while we opted for Florida. Either way we both wanted to get away to someplace warm. In preparation for the trips Karin and I were at the mall shopping. We were looking at lingerie when I held up a yellow bra and panty set. "What do you think? Something for Michael?" "He'd need something up top to fill it out but I like the silk and lace." "We can get him some breast forms to fill it out and complete the look. Do you think he'd wear it?" "Oh, I'm sure he would. He's kind of settled down over the last couple of weeks but I know it's still something he's interested in. Shall we get it for him?" I sensed we had just crossed a bit of a chasm. Did Karin really just ask me if we should get her husband a bra and panty set? I think she did. "Sure we can get it for him, but would I get to see him in it? It is very cute and all." "Can you get the breast forms for it?" Karen asked. "I'd rather not see it on a flat chest." "Yes I can do that. You think a C cup?" "Definitely." "OK, what else shall we get him?" *** When Michael stopped by over the next couple of weeks I was dying to know more about him and his desires beyond what Karin had shared. Just how submissive was he? I unbuttoned my blouse an extra button and made sure to "accidentally" brush against him.
Finally, I thought I had him to the point of no return when he arrived with a hard-on. This was the first time I really got him to open up about his sexual preferences but I still couldn't believe it. He liked to dress as a woman and he wanted to be used as a total sissy slut. As soon as he left, I called Karin and told her what he said.
"Karin, you are never going to believe this. Michael just left but I think he is much more of a sub than we ever imagined. His fantasy is to be used as a total femme slut. If we play this right he'll do anything we want him too."
"Really, what do you mean?"
"I mean, everything from dressing him as a woman to cuckolding him and making him serve you and your new lover. Speaking of that, how is Darrell?"
"Darrell is hot. I've got a date with him next week and can't wait to have him inside of me again. I really couldn't believe how much I loved his big black cock. So what are we going to do to convince Michael to make the change?
"I'm not sure, I'm still working through the details. I've ordered a wig and glue-on breast forms for him, but I haven't figured out how to get him into female attire and playing along."
"Well if you can convince him to keep talking to you, I'm sure he'll play along. Oh, he's just coming in the door now. Gotta go."
A couple of days later I had a call from Karin.
"You're never going to believe this."
"What?" I asked.
"I told you I had a date with Darrell right?"
"Yes, how did that go?"
"Well first, Darrell is amazing. I never knew how horny I could get until you introduced me to him. We did a light dinner and then went to his house. He shares an apartment with Rodney but Rodney wasn't there. Anyway, Darrell began by getting me to do a little strip tease for him. I tried to go as slow as possible but all I could think about was getting his big cock inside of me."
"Finally, when I was totally naked, Darrell pulled me to him pushed me to my knees and made me worship his cock for what seemed like forever. He'd let me work him to the point of getting him off and then stop me and my jaw and tongue were getting sore from the work out. Once he was totally hard, I'd take him as deep in my mouth as I could and still only be tasting half of him."
"So did he give a great fucking then?" I asked.
"Oh my god yes. I still can't believe it. He bent me over the chair and stuffed his monster cock inside of me and then pounded me forever. I came three times before he emptied his cum into me. All I could do was hold on to the chair and cum. It was amazing. Thank you for the introduction."
"Does Michael even suspect?
"Actually that is the funny part. He has no clue, but he ate Darrell's cum tonight. When I got home, he was already in bed and said he wanted me. At first I was worried that my cum filled pussy would be a problem but I just went with it. I told him I was taking charge tonight and made him lie on his back and not move. I gave his cock a couple of licks to get him fully hard and then I mounted him. I'm sure he just thought I was really wet."
"Then you made him eat you?"
"Yes I did. In fact he was begging for it. He said 'After you make me cum, will you make me eat you?' If he only knew. After he added his cum, I straddled his face and made him suck me clean. There was nothing for me to wipe up later."
"Do you think he liked it?"
"Oh yes. He said thank you and everything."
The process on feminizing and cuckolding Michael was going even better than I'd imagined. I couldn't wait to make him my little sissy and my imagination was running wild on using him as a slave and cum slut.
Karin and I spent a good deal of time talking about how to get him to the next step and what we wanted him to do. She was totally taken by the idea of making him a cuckold and introducing him to Darrell. We talked about just how femme he would be for us and whether we should give him a proper name. I asked Karin to tell me about Michael's toys so I could get additional toys for him. The idea of shoving a huge plug up inside of him was really cool. We also had a party coming up shortly and I was hoping to introduce Michael in his new role. First we had to get him to make the change.
A couple of days later Michael was over and I knew everything was going to come together. As before, I'd made a habit of giving him a nice view to get him excited. I wasn't' wearing a bra or panties when he visited next and he was obviously aware.
From small talk, I asked him if he'd like to have me for a mistress. He almost fell out of the chair saying "Yes Mistress". I was hoping he'd go for it but was afraid he'd back out. From his excitement it was obvious there was no backing out. "Tell me about your fantasies" I directed as we sat down to coffee. "I told you the kind of things I fantasize about and that excite me." "Yes, but I'm curious just how far you'll go? How much can I own you?" "Jenny, I've fantasized about being a sissy since I was in high school. If you will have me, I'll do anything you tell me to." "Will you suck cum from my well fucked pussy?" "I would love to clean you pussy after you've pleased a man." "I was thinking men. Would you serve my lovers as well? Let them have you as a woman does?" "I'd do whatever you tell me to do Jenny." This was amazing. Here in front of me was a little sissy slut that I could totally own. I liked being in charge but I could take it to another level. I was so hot I almost made him eat me right here, right now -- but I wanted him, no her, to do it as a woman. Michael was going to need a more feminine name..... perhaps Michelle. "Michael, um ... Michelle, in preparation for getting together on Friday, I expect you to come totally hair free from the neck down. You can use Nair and a razor but I want the hair completely gone. You are also going to need some new lingerie. I want you to have a red look with a bra, panties, camisole, garter and stockings, and a nice pair of heels. You'll want a C cup for the bra." "Yes Mistress. I will get that." "Then, when you come over on Friday morning, I want you to wear a white t-shirt and low rider pants. That's it. You can change your shoes when you got here." "What will happen then?" "You will do exactly what I tell you to or I'll make you wish you had. Agreed?" "Jenny, I can't wait until Friday." When he left my house I was so excited I couldn't help it, I needed to get off so badly. I couldn't wait until Friday either. *** That night I shared my conversation with Michael / Michelle with Chuck. When we started making love my panties and pussy were sopping wet. I sat on my husbands face and made him lick me until I came. I kissed him as he entered me and his face was glistening with pussy juice. The intensity of the lovemaking was very high and it wasn't long before I was coming again and I could feel Chuck spurting deep inside of me. *** There were just a few more details to work out by Friday and I called Karin to fill in the details. I wanted to get him transformed to a she and have him serve a real cock. Tom had Friday's off and I knew he'd be interested in playing and I could tell Chuck what to do. Once Tom had confirmed, the plan was mostly in place. Michelle would be coming over on Friday morning and I would start the make over. I had a plug bigger than what she was currently used to and planned to introduce that as well. Then I could turn her over to Tom and Chuck and see just how willing she was. This would be the big step. I expected Tom to fuck her. Tom loved pounding his cock into little sissies. My bedroom and bathroom were wired for video and audio and I had a digital camera for other parts of the house. We definitely needed pictures of what should be a memorable event and I was pretty sure we'd get some. Karin was getting very worked up with Darrell as well and I'd suggested that while we were busy enjoying Michael that she and Darrell set a date as well. I'd given Darrell a call and suggested the same to him and that perhaps Rodney could join the play as well. I also suggested that I'd like to see pictures of the event and that I wanted Karin to be completely satisfied in the pictures. Darrell said he and Rodney would leave no hole unfilled.
I was already very excited putting things together with Michael but the thought of Karin having both Darrell and Rodney service her at the same time was incredibly hot. I couldn't wait to see pictures of that. Assuming that Michael was the complete sissy I expected, I needed to get him ready for the party on Saturday. Having him made over at the spa would be an awesome first step. I was friends with the owner and knew she'd love it. Then I called Jeff at the Ye Olde Sex Shoppe and told him I'd need a few things. The rest of it depended on Michael and how well he played along.
*** Before I knew it was Friday morning. When I saw Michael walking over I was a bit miffed. The little sissy couldn't even follow basic instructions. I had told him what to wear and he'd put a jacket on over it and the effect of him walking over as my little sissy in a bra and panties was totally wasted. I wanted to show him / her off in public.
When I opened the door and Michael was looking back at me, the name Shelley jumped into my head. I thought she'd be a perfect Shelley and it stuck. From that point on, I really couldn't believe how willing Shelley was or how much she enjoyed being a woman. *** Introduction to Shelley -- Part 6 *** The alarm clock at Anne's went off just before five. "Come on Shelley. Time to get up and get going. I need to drop you off at your house on my way to work this morning. That's a bit of a drive for me so we need to get going. Get yourself dressed and made up for the trip home." It took me a second to get my bearings and roll out of bed. I had my nighty on with no panties. My ass was a bit sore from being fucked hard last night and I could feel the dried cum on on chest and face from Jim spraying me. "Go ahead and use the guest bathroom to get your shower" she said as I worked to wake up. "You don't have a lot of time and however you're dressed when it's time to go is how you'll be going." I dressed in a skirt and blouse with bra, panties, and shoes. Then quickly did my make up. Anne handed me a travel cup of coffee and we headed out for my house. The trip home was mostly silence with a bit of small talk and Anne dropped me in my driveway. When I tried the front door, it was locked and I did not have a key. I rang the door bell. It took a few minutes for the door to open and a part of me could imagine being left out here. Finally the door opened and it was Darrell. He was standing there in muscle shirt and shorts. "Bout time you got here slut. Karin, your little sissy is home." "Well tell here to get your cock ready to go for me." "Karin wants you to get my cock hard for her again. You can come in when I'm hard. I would probably be easier if you were on your knees." I just looked at him, not sure what to do. "Karin, the little slut doesn't seem to want to what she's told." "Tell her to get on her knees and suck your cock til it's hard as a rock and ready to fuck me again." "You heard her slut. Get on your knees. You know you want it." He pulled his shorts to the side and exposed his cock. His limp penis dangled down his thigh about 6 inches and he had huge balls. "Come on sissy, get me hard so I can fuck your wife again." I was both drawn to it and afraid of it but found myself slipping to my knees in front of him. I could smell Karin's pussy as I leaned forward to him and I could taste her as I licked his balls and began to suck him. "Has she got my cock ready yet?" Karin called from inside the house. "Not yet, but she's doing a fine job on the preparation" he said as he grew and began to fuck my mouth with his big black cock. "Well get her ass in here." "You heard her slut. I'll let you slide my cock into your wife's pussy." We walked in the house and up to the bedroom. Karin was on the bed with her legs spread and cum just oozing out of her.
"Lay on the bed." When I complied, she straddled me and parted her pussy lips. Two globs of cum fell on my face. "You're going to love the taste of cum today" she said as she lowered her pussy on my face. "Suck me clean slut". My mouth was full of cum and I did my best to lick and suck all of the cum from her pussy.
"Very good slut. Now why don't you put Darrell inside of me so he can give me a really good fucking? He looks like he needs a little encouragement again. Why don't you wrap you lips around his dick?" I gave him a quick tongue bath and then took him in my mouth. "Ok, now put that beautiful black cock in my needy pussy" she said, opening her legs all the way for him. I popped the cock into her and he sunk balls deep in one stroke. "You don't need to be here for this slut. I'll call you after he spills his cum in me. In the meantime you can go to your room." "My room?" "Yes, your not staying in here slut. I've put all your stuff in the guest room. Go check it out." When I got to my room, I did notice that all of my stuff that had been in the master bedroom was moved. When I opened the drawers to the dresser and looked in the closet, all of my guy clothes were gone. All I had were blouses, skirts, and lingerie. *** To be continued *** Thanks for your comments and reviews. Let me know if you'd like a response (I know not everyone does).
I hope you this was a big a thrill to read as it was to write. I do appreciate feedback on both style and substance and welcome your comments (tastingjenny@yahoo.com)