Mark/Rachel Give up Control

It was early February when Claire mentioned to me that she would be travelling for work the following month. There was a conference in Vegas, and she was taking a team and would be staying there for a few days, probably up to five days including a full weekend but the details were still being nailed down. She gave me the dates, and wrote them on the kitchen calendar, so that I could figure out a few details around childcare and arrange any extra transportation that was needed to get the kids to and from their activities.

I started all the functional detail planning of that week right away. It was no big deal for me to work from home for a short time, and aside from a couple of specific things during the week that required getting our two kids to different locations at the same time, I knew there shouldn't be any problems. Besides, I liked having a little extra time to myself every so often, and I could always find good ways to use the extra solitude.

It was a few days later that I realized the kids had a day off school on the Friday of the week Claire was in Vegas, and that it might be a perfect moment for me to create a bit of 'mental health' time for myself. I'd been needing a little solo time to indulge my fantasy life, and at some point long after the fact, I realized that was exactly how Claire had arranged things, and why it was that specific week that she would be away.

+++++++++++++++++++

Claire and I had been married for about 5 years before I made my first slip up with my cross-dressing habit. I had always managed to be discreet about it, and keep my stash of women's clothes, lingerie, shoes, makeup, and toys tucked away in a small box inside another larger box in the basement, and I only brought things out when I was going to have some time alone - until I wasn't.

Claire had been away for a weekend with some girlfriends at the coast, so I had our rented townhouse to myself. I set myself up for the weekend by pulling out my supplies, and I enjoyed the Friday night dressed up and around home. I went to sleep Friday in a soft satin nightie and the remains of my make up, and having masturbated to three orgasms watching lesbian porn on the internet. I was exhausted, sated, and I expected to have a quiet weekend with lots of time to clean up and put things away on Sunday morning. The problem was Saturday...

I woke up Saturday morning to the sound of my wife gasping in the bedroom doorway and the stunned words, "What the fuck???"

After the typical fear response of covering myself up and trying to hide my face, I knew that I was completely caught out. I had a buttplug and lube on the bedside table, there were stockings and a garter belt on my side of the bed along with a pair of black patent heels that were way too big for Claire. My computer was still open to the porn sites I'd been on the night before, and most telling of all was the makeup I was wearing. In retrospect, it was very poorly done, laid on thick, and as trashy as it could possibly be. I have never been good with makeup, but I have definitely improved as the years rolled on. At that point in my life though, it was all bright red lipstick, thick mascara, and way too much rouge. All in all - whatever I had been hiding from Claire was hidden no longer.

Claire broke the silence with a joke, which I took as perhaps a good sign. "Honey -I'm home", she shouted out like Lucille Ball. "I think we need to talk about a few things, but do you want to talk like you are or would you like a little time to have a shower and come downstairs looking more like yourself."

I was taken aback by her calm, but I opted for the shower and change of clothes before we had any discussion about the state of affairs. I spent half an hour doing a quick cleanup of the room, and showered and removed my make up completely. After making sure that the room looked presentable, and dressing in jeans and a nice shirt, I went downstairs to find Claire in the living room with a cup of coffee waiting for me. She offered me coffee, and told me to bring ALL of my special things down for her to examine.

As I walked up the stairs to the bedroom and my box of hidden treasures, I knew that our future from this point was completely up to Claire. She could accept the realities of what I had been hiding, or reject me completely and that would be the end of our marriage and our time together.

I place the box in front of Claire and took my coffee to sit on the chair facing her. Claire opened up the box and took each item out placing them on the coffee table and the couch. She looked at each piece of clothing, each pair of panties, the stockings and garters, and smiled. "I have always expected you were hiding a little something from me, but this is not what I thought it would be. I was starting to think you were having an affair, and that would have been devastating to me, but this I think I can live with. Why haven't you ever told me you like to dress in drag?" She took out the smaller butt plug and looked at it closely, but gasped when she came to the larger of the two. "You can use this?", she exclaimed. "It doesn't hurt?"

"It sometimes hurts a little going in, but once it's in me it feels fantastic and keeps me turned on for hours," I responded. "The little one goes in easy and quickly, but the other one takes me being turned on for quite a while, and really being worked up before I can enjoy it. I've always wanted to get you to try the little one, but never got the sense that you'd be interested. I know I can put a finger in your ass every so often, but the plug seemed a little different." I was relaxing into the conversation, and feeling encouraged that Claire was asking questions, and was curious about what I'd been hiding and how deep the secrets went.

"And the clothes?" Claire asked. "Have you ever gone out in public dressed as a woman, or it a purely private thing for your own satisfaction?"

"I've worn lingerie under my clothes in public before. Panties and garters and stockings under my jeans, and I've even worn the smaller butt plug out shopping and running errands, but I've never fully dressed or worn makeup in public. In fact, you are the first person who has ever seen me dressed up like that - ever. I've always kept that side of me just for myself. I'm sorry I've hidden it away from you, and I've never liked the dishonesty of that, but it is something I've never felt proud of in my personality. I've been doing it off and on since I was a teenager, and it's always been a shameful thing. I'm trying to be as open and honest as I can right now because I figure that our future is in your hands. If you reject me because of this, I guess there is nothing I can do about it. On the other hand, if you accept this part of me along with the rest of who I am, I don't really know what that might look like either."

In the end, after a full week of non-stop conversation, and some experimentation, and some makeup lessons from Claire, and a demonstration of what it looks like to wear the larger plug (me not her), Claire stated firmly that she loved me regardless of my kinky hidden side, and she still wanted to be with me forever. She also stated very clearly that anything to do with dressing up in public, or anything that might cause problems with neighbours or others was not something she was interested in.

In essence, I could do my thing, but it had to stay private and 'mostly' as a solo activity.

Over the years, there had been a few occasions where that initial rule was broken. I had dressed up for Claire and the two of us had sex in lingerie a few times, and she told me that it turned her on, but she would not encourage or plan anything like that. The thing is that she knew, and we were open about the fact that I like to dress and play while she was away. If I had the time and space, she had no problem with me taking advantage of it any way that I liked, which led me to my current question. What to plan for the time that Claire was in Vegas?

+++++++++++++++++++++

The first part was easy and practical. Claire's parents lived about half an hour from us, and they loved to have the kids over for weekends when the arrangements could be made. With the extra day off, it was a natural time for a little grandparent time, so within an hour I had arranged to have the house to myself on Friday and Saturday. I could easily take Friday off work as I had accumulated lots of time off. When all was said and done, I had two full days with which to play, and no restrictions on my time.

On Friday morning, I fed the kids breakfast and drove them out to the grandparent's place. We had a short visit, and I left my 'agenda' for the weekend so they could get hold of me if needed, and then started the trip back to home. I knew I had a little shopping to do on the way home, so I got started as quickly as I could.

My first stop was at a lingerie store in the downtown Berkley area. I knew what they had and I was looking for a little something to spice up my intimate wardrobe. I was looking for a new bra and panty set, and I had long ago figured out my measurements. I had a pair of high-quality silicone breast forms at home, and I wanted a lace and satin set - preferably with a stretchy thong to cover me at the front. I loved the feeling of the thong between my ass cheeks, and the look of my stockings and garter with matching underwear made me long to be a real woman for just a short period of time. I found the perfect set quite quickly. It was a beautiful turquoise that reminded me of the beach in Hawaii on a pristine day. I paid for them and had them wrapped up, and then took off for the next stop on my journey home. I was just about to leave the store, when I noticed a stretch bodycon dress on a mannequin by the door. It was almost exactly the colour of the new lingerie that I had in my bag, and I knew that I had to have it if the sizing was right. The only snag was that I'd have to try it on in the store to make sure it fit.

It took a little time for me to work up the courage to ask to try the dress on, but I also knew that stores in the city were quite used to odd requests, and that most likely no one would think twice about letting me try it on before buying. I asked the salesperson who I had been talking with earlier if I could try the dress on before I purchased it, and she smiled at me saying that there was no problem, but she requested that she be able to see it on me to make sure of the size. She winked and helped me find what should be the right size before leading me to the changing rooms. As I had already purchased the lingerie, I decided to change into that as well.

The dress fit perfectly, and I knew that it would hug every curve that my breast-forms would create. The thong fit snugly between my ass cheeks and hugged my cock and balls like a second skin, and the bra tickled my nipples, although the shape of it stuck out a little too much under the dress. I thought it would all work perfectly the next day when I dressed up more fully. I poked my head out the change room door and the saleslady was waiting. She tugged at the fabric of the dress, and even reach up under to grab my ass and take notice of the lingerie I was wearing. Once she had her fun, she stood back and declared that the size was right and I should be on my way. I left the lingerie on under my male clothes and headed out to see her at the cash register. I paid and she offered to work with me for a personal dressing session at her house later, but I obviously declined as was on my way. I was loyal to Claire, even if I had my kinks that I mostly hid from her.

The local sex toy shop had a good and varied supply of what I really wanted at that point, so on my way home I made a stop at one of my favourite toy shops. Today I was on the hunt for a couple of specific items. I needed something new for nipple stimulation as the nipple clamps I'd had for a long time had broken recently. I was also on the hunt for a new plug. I was looking for something I could wear for a long time, possibly even overnight, without causing pain or discomfort. There was no need for it to be too large, as my time experimenting with size for my anal toys was long gone. I was looking for something mid-size, with a large base for safe play, and probably something stainless steel so that it could be sterilized really well before and after using it.

The toy stores all around San Francisco carried a pretty wide selection of bondage and anal toys, so it wasn't long before I found something close to what I was wanting. The sales assistant approached me to ask if I needed any help, and so I pointed the clamps I was looking at, and asked what she thought of them. We had a friendly conversation that was completely comfortable and professional, and I explained that I was looking for things that I could wear discreetly for long stretches. She directed me to a pair of vibrating nipple clamps that she guaranteed would stay on under my shirt and keep me excited, both due to the clamp and the vibration. As to a long wear butt plug, my helper blushed for a brief moment before taking me to the right section of the store. She picked up a glass plug and told me quietly, "This is the one I'm wearing right now. I've been wearing it 6-8 hours each day for a week and there's no problems at all. I love that it keeps me thinking about sex, all the time, all day long, and in here - that's a great help for me to sell things."

I took her suggestions and paid for them and left. I thought for just a moment that she was going to say something extra to me, maybe to come on to me or offer a suggestion, but she just smiled as I took my purchases and left.

On the way home, I was tempted to stop and put on my two new purchases, but instead I just made my way the house as quickly as possible, knowing that the more time I had at home by myself, the happier and more satisfied I'd be when Claire returned from her trip.

Pulling into the driveway, I was almost vibrating with excitement. It was already almost six o'clock, and by the time I got inside I had made the conscious decision to relax and go a little more slowly than I would normally have. I had lots of time to enjoy the process of arousal, and dressing, and playing. I dug through the basement to pull out my toy box - it was a little larger and better hidden than the first one that Claire caught me with. I put everything out on my bed and picked out an outfit for the evening, as well as something for the following morning. I laid out my toys, the old and the new, and pondered how to proceed with my evening alone.

After I took a little time for personal hygiene - I trimmed my pubic hair, cleared my bowels, had a shower and washed myself with Claire's lavender body wash - I was ready to really get started. While I was in the shower, I planned how to move slowly through the steps of arousing myself and keeping edged. I knew that I would bring myself to orgasm by the nights end, but I wanted it to take a good, long time.

I started with the easy decisions. I knew I would fully dress the next morning, and had already decided to wear my new lingerie and dress, but for the evening I was sticking with older clothes and lingerie and newer toys. I lubed up a mid-sized silicone butt plug and gently worked it inside me. I'd stretched myself out a little in shower, so it went in easily, and I gasped a little as it slipped into place. It was large enough that I could feel it's presence, but not enough to cause a complete distraction from the other tasks at hand. I chose a black thong from the bed, and took a look in the mirror as I pulled it up and over the base of my plug. I loved the feel of the thong enveloping my cock, and holding the plug just a little more solidly into my depths. The plug was really just a warm up for the new toy I'd purchased that I would start wearing in the morning, but I knew that with it inside me, I could orgasm in a heartbeat if I just let myself go.

When I clamped my nipples with the new clamps, I spent a few minutes playing with my hardened nipples. They were always sensitive, and Claire loved teasing me by licking and biting them during foreplay. There are times I wished she would tie me down and immobilize me and just play with my nipples until I came from that sensation alone. I turned the vibration on for just a moment - as a tease for the next morning - but wanted to keep things calm for the moment so as to make my evening last as well as possible.

I put on a black bra to match my thong and help keep the nipple clamps in place, and pulled up a new pair of black thigh high stockings and attached them to my newest high waisted garter belt. I'd recently purchase the garter belt online from a retro lingerie store, and it took some time and effort to attach all eight garter straps and make sure they were evenly distributed around my legs. It may have taken a little extra time as I was watching myself in the mirror and continued to stroke and tease my hard cock through my panties, occasionally giving the base of my plug a little tug to continue the process of feeling every nerve in my body come alive.

Once the garters were in place and solid, I pulled on the last piece of clothing for the evening. This one I borrowed from Claire, but I'd bought it for her as a gift for Valentine's Day the previous year. It was a long satin and lace nightgown, black with red hearts all over it. It was pretty, and romantic, and I loved the feeling of the bottom rubbing against my nylon covered legs. The satin was cool to the touch, and I lingered over the feeling of how it clung to my ass and rubbed me as I moved.

Once I was fully dressed for the evening, I put on a pair of black heels and moved down the stairs to the kitchen to get a little something to eat. I'd taken a few minutes to close all the blinds when I got home, so I knew that I was safe to move around the house freely dressed any way I pleased.

The night progressed slowly, with some internet porn and reading erotica online. I connected my laptop to the big TV in the living room and set up the surround sound so that I had the sights and sounds of sex washing over me, encompassing me in desire and lust. I wasn't in a hurry to do anything, and I kept myself aroused searching whatever was interesting to me in the moment. I kept falling back to lesbian bondage videos where beautiful women in latex dominated and strap on fucked their bound partners. I dreamed of being the bound, dressed, clamped and teased woman who was the submissive in those videos.

After a few hours of keeping myself teased, tempting myself to go further and finally cum, I ran across a video of a dominatrix lovingly dressing a man in lingerie and tying him to a bench to fuck him with her strapon. It was the last step in my fantasy evening, and as I watched his eyes get big as she pounded in and out of his ass, I felt my resolve slip away and I exploded and filled my panties with cum. I lay panting in a puddle of lust as the video ended with the man on his stocking covered knees licking the asshole of his mistress, cleaning her pussy, and eventually lying beside her while she stroked his hair lovingly. I knew that my dreams overnight would be of submission, I just wished that Claire was inclined to be truly dominant in our relationship. As it was, I knew that I would have another day tomorrow to keep my fantasy life alive and kicking, and I just needed to plot how to best take advantage of my time alone.

I left my laptop downstairs, connected to the TV as I knew I'd end up back there at some point the next day and took myself to the shower before bed. I wanted to clean myself up well so I could start the next morning on my full transformation into my crossdressed self. During our week of exploration, Claire had named my alter ego 'Rachel' and from that point on, that was how I thought of myself when I was fully dressed. When it was just a few moments with lingerie and toys, I was always Mark, but the wig and make up make it far more real to think of myself as a woman.