Mark/Rachel Give up Control

When I pushed my fingers into Claire's dripping pussy, she whimpered a little and moaned, so I knew that I was on the right track. It wasn't the physical things that Claire was missing, but being able to let herself be taken and controlled.

And that was how it started. Claire submitting to me sexually, but both of us always keeping up appearances and continuing on with our more professional relationship. I enjoyed taking care of Mark and Claire and began to feel a real friendship with both of them, and when opportunity arose, Claire and I kept up our sexual relationship with her occasionally advocating for Mark to join us in a threesome.

I had always been the dominant force sexually in most of my relationships, and I'd been equally willing to fuck men and women as I was learning my own sexuality. I'd been primarily with women for many years, but had no real problem with the idea of being with a man again. The fact is that most of the male students and people I was around were just not that interesting to me. I wondered if Mark might be a little different, and I knew he liked to experiment and I was certain that he was a closet crossdresser, although I couldn't be certain if that was for his own enjoyment, or if it was something Claire pushed him into. From the ease and speed that Claire allowed herself to fall under my control, I could only guess that Mark was a sissy all on his own, and that Claire probably couldn't take him under her control although it might be what Mark really wanted.

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And now I could see all the pieces falling into place. As soon as I heard the click of heels coming down the stairs, I understood what I was about to see, and I needed to decide how to respond to the whole vision. I had come prepared for a variety of realities, and I had an overnight and toy bag in the back of my car. I knew that Claire wanted Mark and I to have some time together to get comfortable. I planned to seduce Mark quickly and was led to believe it would not take too much effort, but seeing Mark fully dressed impacted my plan for the seduction piece of the day.

Mark was lovely. He had obviously taken great care with his clothes and makeup, and although I wasn't a big fan of blond hair, there was no denying that it was cute and it suited him. He was wearing a snug fitting dress that barely covered his ass, and there was a cutout that hugged his breast forms and showed off the lace of his bra. He was wearing stockings, and I assumed some sort of waist cincher or corset to tighten his tummy, and I could see the outline of his garters on the skirt. He was obviously very comfortable in his clothes, but less so in the heels as he was being very cautious with the stairs. He probably hadn't had too much time to practice in them. The makeup was simple, but done well. I thought how much I'd like to take some time to dress him up and play with him like a barbie doll, and try out different styles and outfits on him to discover the extent of his fetishes. I also knew I'd want to give him a little more cover if I was going to take him out for lunch...

I took a deep breath, relaxed and smiled before I spoke. "So Mark - or do you have another name that I should use for you while you are all dressed up?"

Mark looked at me with his eyes a little bugged out. "My name is Rachel", he said quietly.

I smiled, both at his honesty and at the memory of where the name Rachel must have come from. When I was in the process of seducing Claire, I asked her if she had ever been with a woman before. Her only experience had been in her first year of university when she was seduced once by her very lesbian roommate. She hadn't followed that up with any further experiences after she started dating Mark in her Junior year, but it was a good sexual moment in Claire's life and she had obviously named Mark's feminine persona accordingly.

"Good. Thank you. Rachel - I think you should know that although you came down here expecting to find a present on the table, you are actually the present that has been laid out for me to play with. I knew that you crossdressed a little, but I didn't know that you were actually good at it, or whether you only did it for Claire, or if it was for your own pleasure. Now I know that you have done this quite a bit, and probably for a long time, and that will change how I provide your 'present'. I think we need to talk things over for a little bit, and I think that I know the perfect place for us to have a conversation. You are going to buy me lunch at a lovely little café just out of town, and I'll tell you all about how the next couple of days could go for you."

"For the short term - please come sit down."

Rachel sat in the chair across from me. It was obvious to me that she was wearing a butt plug as she shifted herself into position a little when she sat. She crossed her legs demurely, and looked at me waiting for me to take the lead in the conversation.

"I think it's very important for you to know two things right away, just so you can start to relax a little. 1. Your secret is completely safe with me - and obviously Claire wanted me to catch you in the act of dressing. You have nothing to be afraid of, and I won't tell a soul about your secret hobby. 2. Claire and I have been fucking for a few months now, and she has been trying to get me to include you in a threesome for a while. I've always said no, as I didn't want to be in the middle of your relationship or cause tension between you. I think we are past that point now, so I think it's important to have all our cards on the table.

"Now - I need for you to do something for me. Go out to my car and get the small suitcase from the back seat. I think I'm going to need it. After that, I want for you to show me around your hidden stash of women's clothes and toys, and we are going to spend a little time exploring before we go out for lunch, in public. I'll need to adjust your make up a little, and probably find something for you to wear that is a little less - obvious - but I love what you have done with yourself, so you can mostly go out just as you are. Now go!"

While Mark was working up the nerve to step outside and get my bag, I considered both my own immediate desires, and also what I'd been looking for in relationships for a large part of my adult life.

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I had always wanted to be in control, and had learned the role of the dominant early in my sex life. The only time I'd dated anyone for an extended period of time who I could not completely dominate was in my first year at Berkeley.

Her name was Sylvia and she turned me on from the moment we first met in the dorms. It took a few months before we ran into each other at a party, and through some flirting and drinking, we ended up back in her room that night. Sylvia was obviously and openly lesbian, and dressed and looked like a fully dominant woman, but in bed she was hesitant to fully take control, but never really relished the submissive role either. We had a good time together for about a month before I broke up with her because I realized that I absolutely needed to be the dominant sexually, and was unhappy with anyone who would be anything but blatantly sexually submissive to me. The only lasting impacts of our relationship were some good memories and my pierced nipples. Sylvia convinced me to get mine done to match hers. Initially it was just a small stud, but as I got a little more daring, I had a small collection of dumbbell clips, rings, and other nipple jewelry. I loved the weight of the dumbbells as long as I was wearing a good supportive bra, and I wore them at any time my situation had a chance of ending sexually. I'd been trying to convince Claire to get her nipples pierces, but had no success so far. Maybe I'd have a little more luck with Rachel...

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Rachel came back in from outside and interrupted my thoughts, bringing me back to the present. "Carry my bag upstairs to your room and show me your collection," I commanded. We walked upstairs and entered the master bedroom where I could see the laptop and lingerie collection laid out on the bed.

"Is this everything Rachel, or do you keep another stash somewhere that you haven't got out yet? Do you just wear your own clothes, or are there some things of Claires that you wear as well?

Rachel answered, trying unsuccessfully to mimic a feminine voice. "This is most of my lingerie, but I have some clothes in another spot. I wear some of Claire's larger, looser clothes sometimes, but I like the things I've bought for myself better. I like my clothes tighter and silkier than the things that Claire wears generally, and our sizes don't really match except her shoes. I can wear most of Claire's shoes, but particularly the higher heels, but I don't get a chance to wear them very often."

I laid my suitcase out on the floor and opened it up. I had a small variety of clothes and lingerie on one side, and the other side of the case had a variety of sex toys and bondage gear that I thought might come in handy. The one thing that I didn't bring with me was a strap on, but fortunately I knew where I could find on in Claire's hidden things. I hoped that by the end of the weekend, I'd have good reason to find the strap on and fuck Rachel silly, and maybe Claire as well.

"We need to find something a little more appropriate for you to wear out for lunch. I like the outfit you're wearing, and you look quite genuinely slutty, but we need something just a little more demure for being out on the town. Why don't you start by taking off your dress and shoes, and getting me the rest of your clothes and we'll pick something out for the day."

Rachel took a moment to evaluate her situation, but I could tell how hard she was getting under her tight dress, and I knew that she would follow along with me wherever I went at that point. I appreciated the fact that as Rachel stripped her clothes off, she moved with some small level of grace. She bent at the waist as she pulled down her skirt, and showed me her lingerie and the wide looking plug in her ass. I reached out to touch her gently before she stood up, and ran my hand along the tops of her stockings and up into the crevice between her cheeks. When she pulled off her dress, she stood in front of me as a vision of turquoise satin and lace.

She left the room and led me to the spare bedroom and pulled out the middle drawer under the bed. She had to get down on her elbows and knees in order to pull off the drawer and reach through into the hole under the bed. She pulled out a large bag that I assumed was stuffed with a variety of clothes and toys. I admired her ass as it stuck up in the air while she reached under the bed. I was getting turned on, and I felt the flush of power come over me as I pulled Rachel slowly into my web.

I sat down on the bed before she had a chance to get up and told her, "While you are down on your knees, I think I have a task for you to accomplish before we get you dressed and ready to go out." I pulled up my skirt, and pulled my thong to the side, and simply said "Lick my pussy and make me cum."

Without a word, and surprisingly without hesitation, Rachel leaned herself into my wet cunt and went to work. I'll be honest and say that she was a better pussy licker than I thought she would be. She took her time, and licked around the outside of my cunt. She kissed my inner thighs gently, and took time to breath heavily on my clit. When she finally dove her tongue into my centre, I was turned on to the point that I was leaking all over her tongue and face. I let her play for a while, arousing me and holding me out just a little, and finally I directed her towards my clit and held her head in place. "Flat of your tongue", I gasped out and I came just after Rachel followed my command. I was shocked at how easily the orgasm came, and how intense and quick it was, like a little electric shock to my system, and I knew that there would be more to come later, but for the moment there was a bigger job to do.

When I had calmed down from my orgasm, Rachel and I took a few minutes to plan out our coming adventure. She was still on her knees in front of me, and her lingerie was stunning. Aside from a thin line where her forms met her real skin, and the obviously male body hair all over her, she was perfectly proportioned and made a beautiful woman. I smiled thinking about the possibilities we had ahead of us for the rest of the weekend, but first we really needed a longer conversation to lay out our ground rules.

Rachel and I took the clothing bag back to the master bedroom and she laid out her clothing options for me. I loved the sway in her ass that came from walking with her wide plug inserted, but I knew that I wanted her to be more comfortable and less obvious while we were out. Choosing clothes and toys was going to be a challenge.

I looked inside my suitcase and pulled out a fairly large steel butt plug with a comfortable base that fit snugly between the cheeks. I sent Rachel to the bathroom to switch plugs before getting her dressed for the afternoon. I offered to help with switching plugs but Rachel blushed and declined saying that she could manage that on her own. When she returned, I admired the base of the plug under her thong panty, and began to imagine myself opening her up with a strap on in a more vigorous way.

After looking through the clothing options that Rachel presented, I chose to put her in a mid-length red dress with a halter top that came up around her neck and clung to her body, showing off all her self-imposed curves. I knew that her voice would be a giveaway, but I wasn't planning to let her talk very much while we were out anyhow, and I thought with the dress that she could wear a scarf of something to give her a little extra protection against being caught out. Honestly, the Bay Area was about the most open place for transsexuals and crossdressers in the US, but I still wanted Rachel to be comfortable and feel safe while we were out to lunch.

She borrowed a pair of red heels from Claire that were a little more stable and low than the pair she had been wearing when I arrived. By the time I touched up her makeup a little, and changed her lipstick to match her new outfit, Rachel was all ready to go. I directed her to take a few moments and look in any mirror that was available. There was no way that on first impression, anyone would see Rachel as anything other than a hot MILF out with a younger friend or family acquaintance.

Rachel was getting obviously nervous as we prepared to go out, so I had to try to calm her down a little. As she moved down the stairs, I stared at her ass and felt myself getting wet with anticipation of what was ahead.

We left the house and I let Rachel drive as her car was much nicer than mine. While she was driving and taking directions out the café, I pondered how I should direct things for the next day or so.

When we got to the café, it was almost 1:00 and the parking lot was virtually empty, which was perfect for our afternoon adventure. We were seated quickly in a corner table, and we looked over our dining options. Rachel was paying, and I felt the need for a drink, so I ordered a glass of red wine and Rachel followed suit. We ordered light lunches, salads with chicken, and Rachel seemed to be copying or imitating all of my decisions. Once our order was in, our conversation started down a more sexual path, with me leading the way once more.

I started. "I think that for our lunch date I will ask you questions and your job is simply to answer them honestly and completely. You are under no obligation to go into more depth than I ask for, but I understand if you have stories to share with me and things that you need to get off your - chest... To start with, have you ever been out in public dressed as Rachel before?"

"Never as Rachel. I've worn lingerie and occasionally a toy out in public, but nothing that would be evident to other people anywhere outside of the house"

I continued. "Obviously Claire knows Rachel, but are you lovers, or does Claire just acknowledge your existence when she is away? I'm curious to know why Claire hasn't encouraged Rachel to play with her more often, as I know full well that Claire has no objection to playing lesbian games."

"Claire knows that I like to dress up and play, and that I like being taken advantage of and told what to do. I think that we are both ultimately too submissive to dominate the other and make any relationship between Rachel and Claire a reality."

"When you say you are submissive, what exactly do you mean. I am very dominant sexually, as you've probably already figured out, but different people have different ideas of what it is to be a submissive. I know that Claire prefers to bottom when we fuck, but how are you when Mark and Claire are together. Is one of you always in charge, or does it switch around?

Rachel replied, "It switches around. Neither of us generally likes to take control, but usually one of us will give up more control than the other, and then things progress from there."

"When did you start crossdressing?"

"I had the usual story - the one I've read many and heard many times. I started with laundry when I was a teenager, trying on panties and lingerie in the bathroom, and sometimes masturbating. It progressed as I got older, and I've purged my collection of feminine clothes a few times over the years, planning to stop. Ultimately, my femininity is a part of me that I don't really want to let go of, and now that Claire knows about it, I don't feel like I'd ever really have to stop, even if she doesn't want to participate."

"Have you considered transitioning, and living as a woman full time?"

"No. I've never really thought about it. Claire and Mark have a great relationship, even if some stuff stays a little more hidden than I'd prefer. Rachel gets her time to play often enough to keep her satisfied, and the balance is OK enough that things are good overall. I think Rachel would like to be more a part of our sex life, but Claire and Mark are really good together and make each other happy, and I am happy as both a man and sometimes as Rachel. It's not perfect, but nothing ever really is, so I'm not up for changing anything permanently."

"OK - thanks for the honest response. I can tell that you've thought about some of these issues before," I replied. "Next question. Have you ever considered paying for someone to help you fulfill some of your Rachel fantasies? I'm not sure if Claire would support the idea, but would you ever be willing to go that route to help Rachel understand herself better."

"I'd probably be willing to pay for some help with the feminization side of things, helping me with clothing choices and working on my voice or movement, but I can't imagine paying for someone to do the sex side of things, or dominate me or work on making me more submissive. Mark is a pretty 'in control' kind of guy, aside from the bedroom, and although Rachel might submit to someone for the experience, I think Mark would have a harder time seeking that out. It's weird to talk about my two personalities as different people, but that's kind of what it is like."

"Rachel. How does the plug in your ass feel right now as we are sitting in a café talking about sex? Does it arouse you, or make you uncomfortable, or distract you?"

"Honestly, I forget it's there at times, and then when I remember it completely turns me on. As Rachel, I sometimes get lost in the persona and forget about my body a little, but then if I shift around a little, the weight of the plug shifts and all of those sexual feelings wash over me. Part of me is caught up in the conversation with you and the reality of being out in public as Rachel, but part of me is caught up in a very sexual moment and completely distracted by the feelings in my ass, and the stockings on my legs, and the panties covering me. I feel the makeup on my face and the wig, and am completely turned on by all of the variety of new things happening. All of that while being somewhat wrapped up in thoughts about where all of this is heading. There are a lot of experiences that I'm in the middle of at the moment, and they all overlap and expand on each other. I'm having a hard time keeping it all straight, but I like it all. Thank you for being willing to take me out today."