When Annie made Me Lucy Pt. 10

Authors note: This is best read in the right order. Annie and I met at work and found we both share the pleasure of sex in lingerie. I have already spent the weekend at Annie's fully dressed, been out as Lucy, had sex at a charity auction and licked my cum from my girlfriend. A hypnotist friend helped Annie and I feel our false additions are real before Annie fucked me... and the next stage starts as I go to work as Lucy, start to leave drab behind and experience bondage for the first time.

Note - this will always be a story back and forth. It has annoyed some readers, sorry about that but its what it was and it would not do justice to my lovely co-writer to try to only give this from one perspective. If that isn't for you... pass on by

Annie

The morning seems like a crazy rush even with all the preparation that we've done. I carefully help you with some of your makeup though you're getting better at it fast. You look delicious but businesslike in the outfit I picked for you. I even gave you a pair of my own panties to wear as a special surprise on your first day. Breakfast is a fast affair with Marie wishing you all the best on your first day.

Getting into your car is a bit of a shock, the feel of the seat is different when you're wearing women's clothes, heels, and wig. Using the foot pedals in heels takes you a little bit to figure out but then you're on the road. Lucy is driving to work. You are sitting at stop lights with people all around you who can see you as the beautiful woman you are. A few look your way but none that know your secret, only those who are attracted to you.

Pulling into the company parking lot, your nerves get quite agitated. Stepping out of this car will be the first time you've done so on your own, as Lucy, as a woman in public, and expect to be accepted fully as her. You take a deep breath, feeling how wonderful your breasts feel in the corset, how wonderful all the pretty lingerie and clothing feel to wear. You have to maintain discipline to keep your cock from getting too excited though you feel a half-hardness in your panties and a warm arousal glow in your body, to your cheeks, to your sensitive nipples, and even to your 'pussy'. Are you ready to take the plunge?

Lucy

What a day and a night we had but as I awake I am both apprehensive and excited about our new adventure... Lucy Ericsdottir starts as an intern to Annie - will she succeed? Last night I drifted off completely in Lucy mode, my breasts slightly aroused by the sensual material and my cock by the feel of your breasts against me but now I watched you select my outfit, a nice gesture for my first day but I know I will need more of my own wardrobe if I am to continue.

The morning is a whirl, and I check my makeup after breakfast for the last time. Purse and handbag, I kiss you briefly knowing we will meet in different circumstances shortly. Even Marie coyly kisses my cheek and wishes me good luck. I think about what you said about sharing adventures and lean in to whisper to you, "I am always yours, and our adventures can be separate or together as long as we tell each other... but can I ask one thing? If you need another real cock in your delicious pussy I get to know in advance?"

And with that I am gone, walking out to my car in full view, Lucy, Annie's girlfriend going to work.

I love the drive but it's over too soon and parking up feels weird now I am at my work but not at all like I left it barely 3 days ago. I don't hesitate and though there might be a telltale bulge I try to control it as I lock the car and head to reception. Walking in heels is already natural to me and I barely think about the slight sway to the hips and the slightly shorter steps I take that emphasise my femininity. No one seems to bother me as I cross to the entrance. The first shock is seeing close colleagues of my old self coming to the main doors of the office block at the same time. Jack and Katie both work alongside 'me' and I watch nervously as Jack smiles, opens the door for me and allows me in without a blink of recognition. They follow me and Katie smiles, "Hello, you a new face around here? Can I help?"

This is it, a tester again, there will be a lot of these today and it's good as it keeps my excited cock at bay.

"Hello, Lucy Ericsdottir, I am starting as an intern with Annie today so I got here early. I just have to report to reception and she will meet me there"

Katie smiles again, "Sounds a great opportunity, follow me and I will take you up, it's easy but always nicer to have someone with you. I love the skirt, by the way."

Jack had headed off but Katie and I clicked our heels across the tiled floor and entered the elevator. As she hit floor 4, which I knew was Annie's, I thanked her for her compliment.

"Thanks," I said, "It's borrowed to ensure I make a good first impression, but I do love the material and the fit. Your blouse is lovely too, the colour really suits you," and there I was, Lucy... chatting to my old colleagues as if we had never met. I barely spoken to Katie before, she seemed too aloof and out of my league when I was drab, but here we were, chatting away and making small talk until the elevator reached the right floor.

"Thanks Katie, you have relaxed me so much, catch you later perhaps," as I brushed her arm did I see a slight flush? Mmm, nice figure I thought as I turned and introduced myself to your PA.

Annie

I arrive soon after you and we have a kick-off meeting in my office. I can't help but touch your leg as I 'show' you the computer set up and discuss what I'd like you to work on. You'll have a desk just outside my office so in view of everyone walking by or coming to visit me. I make sure you're doing well and I'm delighted when you gush about how well it's going. Your mannerisms and voice are becoming second-nature to you and since you happen to have almost no Adam's apple bulge, there is nothing to disturb your life as Lucy.

The day starts to get busy and you're able to see me launch into my work. You'd never really seen what I do and are impressed by the seniority of the clients I work with and how well I know our systems. In fact, I get so busy that I have to apologise that I can't take you for your first day lunch as I'd promised. Luckily Katie had to see me for something and volunteers to take you out.

Lucy

I have had a whirlwind of a morning and am impressed with how you, my mentor Annie, cope with what comes at you. You are too busy to make lunch on my first day but Katie, that lovely lady from my old division, is somehow available and I wonder if she has clocked anything?

Just before Katie arrives you sneak a stroke of my thighs under my skirt and whisper, "So good, darling, tell me how lunch is."

Well.. lunch was a dream. Katie showed me the little coffee place that does great sandwiches just around the corner, and whilst I have been in so many times I was not recognised at all. My confidence grew and I found myself chatting about all sorts of girly stuff with Katie - makeup tips after lunch, which men to avoid sitting close to! The office and why she loves working here. I ask about partners and she is coy, saying no-one at present and I swear she is flirting! I let her know I have a partner (I can't tell her it's the gorgeous Annie) and that seems to kill the conversation a little. I feel slightly disappointed so I flirt a little, hinting that we are a little exotic in our play and I see her eyes glow again.

All too soon it's back to the desk, but not before Katie kisses my cheek and brushes my arm lightly, saying we must lunch again soon.

Annie

As the afternoon winds on, you almost lose yourself in the work. It is only after a period of time that you realise that you've been happily on 'auto-pilot' behaviourally as Lucy without any worry of 'slipping up'. It's just natural now.

You knock on my door as the day starts to wind down. "Do you need anything else Miss Schwartz?"

"Come in. Close the door."

As soon as the door is closed I embrace you and kiss you. My kisses are restrained in the way you're learning so as to not make a mess of your make-up but my tongue is active.

"I've wanted you all day," I whisper, my throat husky with my desire. "I got a call from a special friend who wants to come to the house for dinner. I told him I'd have to check with my girlfriend first..." We keep kissing and touching each other and your cock is rock hard, straining in the tight panties I laid out for you in the morning.

"Jack and I have... an understanding. We have 'benefits' as you probably have guessed. I don't want you to think that you aren't rocking my world, but he only comes through town occasionally and I'd hate to miss an opportunity to... well..." And you see my face is red with blushing.

"What is it, my love?" you ask, caressing my cheek.

My hands pull up your skirt to touch and fondle your cock in your panties. "Well, if it is okay with you, I'd love to have you filling me up... and Jack inside me too..."

Lucy

Our kissing reminds me of how much you turn me on, and wearing your panties, well all of your clothing, turns me on even more. When you mention a man, Jack, and you blush I want to know more.

"And I thought you were a girls girl...," I smiled, "so tell me more about him? You know we are new and will explore, but I am not sure if I am ready to be Lucy with a man around. When you say you want us both filling you...how?"

Annie

"Well, I am a girl's girl," I smile naughtily, "But I can enjoy the other side too." I fondle your hard cock to accentuate my point. "Every once in a while, when Jack would come through town, I'd enjoy him for a night or two. Marie particularly enjoys him. I know you're hesitant about being involved so if you are okay, I can spend some time with him without you but you know I'd much rather have you with us."

"Well... to be honest I was thinking you might be in my pussy and he would be in my mouth... or if I get super adventurous, maybe him in my ass... I can only imagine how amazingly full that would feel! And, you know, we see where it goes from there, what you think you want to do once we're playing..."

Lucy

I draw my breath as I realise your adventurous side is really coming out now.

"Sorry sweetie, I wasn't thinking quite like you meant," I said with a rueful smile. You stroked my cheek, and waited for me to go on.

"I love how varied your approach to sexy fun is, but... I don't think I am ready for seeing a naked man and his stiff cock. I think it turns me off when faced with it and I wouldn't want not to be able to perform... and..." and I was watching you nervously, aware we were still at work, "I am not sure as I am ready for a man to see me yet... it's a bit soon... I mean, Marie is fine, she understands... "

I realised I was gabbling a little so stopped and took a breath.

"Annie, I don't want you to miss your night with him because of me, perhaps I can stay out of your way in another room or swim whilst he arrives and you head to yours... and you tell me all about it tomorrow?"

Annie

I nod and smile. I'm tempted to call it off with Jack but if you and I are going to work like I want us to, it's better to be clear about expectations.

"I'd love to tell you all about it in the morning," I give you an impish wink. "And if you'd like to spend time with Marie this evening, that might be nice for both of you. Or you're welcome to make yourself more at home... I hope you'll consider it home someday soon..."

Thoughts of moving your stuff from your old apartment to my house dance through my mind and I picture you in short shorts with a cute short top tied off under your breasts and your hair in a sexy pony-tail to 'work'.

We kiss and hold hands for a few minutes before we open the office door again. "Glad you had a good first day, Lucy. I'll see you tomorrow," I say clearly for anyone else still around the office.

We head back to the house separately and reunite there. I'm giving Marie some suggestions for our dinner when you walk in the door, a business woman conquering the world in style!

"Jack won't arrive until about 8pm so we have time for dinner and relaxation. If you want to be swimming or off with Marie when he arrives, I understand. We'll keep to ourselves but I will make sure you can come to bed with me by 11pm," I say, a little nervous that you're okay or not okay with this as I try to focus on the logistics of the evening.

Dinner is light and refreshing and shows off Marie's considerable culinary talents. We both give her praise that makes her blush in her proper yet sexy maid's uniform which she prefers as her daily wear.

I disappear around 7:30 and you hear the doorbell promptly at 8pm but don't see us. Jack leaves shortly before 11pm and I retire to our bedroom to wait for you to join me....

Lucy

I am pleased that you felt able to have Jack over even though there is an unmistakable twinge of something - jealousy? envy? - that tells me I am getting rather attached to you. It's weird, if you had said Jacqueline I would either have joined you if invited or wished you well and been envious that you were exploring her as well as she you... but a man's cock filling you, maybe his cum left behind.... something different. I will get used to it, am sure, but I secretly cross my fingers and hope my reticence doesn't put you off.

Dinner is fabulous and Marie seems to pay me a lot of attention, making me wonder if you had explained our evening. When you disappear I give you a hug and a long kiss... I hope it tells you Lucy is definitely getting more attached to you.

To pass the time I find the swimming costume I used and tucked my cock carefully into the shimmering bottoms, covered my tingling boobs with the top, tied my hair back and swam for 40 minutes or so, lost in my thoughts, trying hard not to imagine him fucking you but failing... hey ho, seems I have fallen for you.

Marie helps me out and dries me off, brings me a drink out by the pool and wordlessly kneels at my feet and starts to peel my bottoms off. At first I am startled but I lift my cheeks and she swiftly pulls them down my long legs and away.

"Mistress Annie will want you to last a long time when you go see her, so I think I should take care of your first load it would be an honour to do that for you Mistress Lucy"

I knew better than to argue, and let Marir do her work. Her hands massaging my thighs and calves first and then working toward my stiffening cock felt delicious - different to yours but arousing. I laid back and moaned as I felt her lips settle on my cock head and seek the precum before taking just the head in her mouth. She was soon taking my length into her whole mouth, the head just nudging her throat, my moans telling her I was enjoying and getting close. Finally she slipped all my hot hard cock into her throat and her lips were on my pubis, her hand lightly stroking my balls and a finger reaching for my rear hole, my pussy, no longer virgin after your exploits.... fuck, that felt good and without much more encouragement I exploded. My first shot went straight down Marie's throat but she eased off quickly and took the rest in her mouth, savouring it as she drained me. She looked up and showed my full load before swallowing it down.

"Fuck, Marie, that was just what I needed, if Annie has anything left to give or wants anything from me when he leaves... I stand a chance!"

"You are welcome Mistress, I love to serve and keep you and Mistress Annie happy"

Annie

You come upstairs and to the bedroom. The smell of sex isn't quite hidden by my perfume. I'm laying on the bed in a satin robe, one breast bare, hair mussed. I smile and reach out for your hand and bring you to sit next to where I'm laying. I caress you and kiss you when you lean down.

"Are you ready for bed, my love?" I ask, my fingers wandering up your back in a suggestive manner but looking to see what you desire.. to talk... to sleep together... to be frisky..

Lucy

"I want to sleep with you tonight, as usual... and I like that phrase... but... I am in uncharted waters here, gorgeous girlfriend. Please understand I want to be relaxed about our sexual adventures together but... a week ago I lived life as a normal male and the idea of another man fucking my girlfriend is one I would have struggled with. I am becoming more and more Lucy, your lesbian girlfriend, but I have a way to go... and it's going to be a long road if you can wait around... "

You squeeze my hand as I lie on the bed next to you. You have a satisfied glow which has not come from sex with me, and I can see that whilst this was fun for you there is a little concern hiding away. That is something I am pleased to see in a way, it tells me I am important and you are balancing the old and the new still too.

"I think I want to hear about it," I continue carefully selecting my words,"but I don't know if I want to go where he has just been... that's between you and him and you should sleep with the feeling of your lover and not rid yourself quickly of something you really wanted. So... tell me what and why Jack gives you something that you have not been able to get elsewhere... and perhaps tomorrow we can see if some after work Lucy sex can work too... is that ok my love?"

Annie

"I'm here with you for the long road together, darling. And if you decide Jack is something you can't get comfortable with, I understand and I wouldn't see him any more. I hope it goes the other way but that will take time if it happens at all."

You lay down and back against me, in my embrace and ask your questions.

"Jack and I have a history most of all. I mean he is a very skilled lover who happens to have a beautiful cock but I think it is our history that makes him a comfortable 'place' to visit every once in a while. There were times in my life I felt I was heterosexual and denied my true orientation but they weren't terrible. I mean I love your cock very much and I would miss it if you never used it like a cock again. So, it isn't like he gives me something I can't get elsewhere physically but it is hard to find old friends who you've shared the road with for a while."

"Now if you're going to make me wait until after work for my lover, I think I'll be pretty ravenous," I tease. "I might get a little crazy with you." I kiss you briefly, then more fully. We kiss for a while, comfortable together on the bed.

"Time to sleep, my love, shall we change into our nightwear?" We get up and I open one of my lingerie drawers, letting you pick which colour slip and panties you want tonight or if you want to wear something different that works as well. I ease off the robe to stand naked before finding some satin panties and a matching slip for myself.

Once we get under the covers I take you in my embrace again and happily fall asleep together....

The next morning isn't anywhere routine yet but repetition makes things go a little easier... showering, makeup, dressing, breakfast, driving to work, settling in for the work day. I'm working hard to not send off signals that we are lovers but it is hard. So I take some meetings on another floor or have you do individual tasks leaving us not together for most of the day.

When the end of the day rolls around, I stop by your desk, asking if the new PC issue got worked out, the status of one of the assignments, and if you had any questions. Before I head into my office, I hand you a small manila package with something in it. I wink at you and go into my office to catch up on things I've missed during my meetings.

You carefully open the package under your desk and see a butt plug, a small container of lubricant, and a note. "Slip this in now for your ride home"

Lucy

I am grateful for your explanation before we sleep, good friends are hard to find and they need to be kept. It makes me realise how much the change to Lucy will be difficult for me. I have not yet made close friends in this place but there are two or three people who it will be difficult to not see again. And in thinking that way I realise I am getting myself in the place to be Lucy full time, and that both shocks me and excites me.