I inherited Monica by default. When I bought my apartment, the woman who was selling asked if I’d mind keeping her on as my cleaner. “She’s really cool, very good and intensely loyal. You’ll love her.”
I’m a pretty tidy person, but being new in town I thought it seemed like a good idea.
“Yeah, sure. We can do it for a month and if she works out, then I’ll keep her on.”
I’d been in the new place for 5 days, getting things together, laying out my workspace and unpacking when I heard the doorbell. Aside from food delivery people, this was my first real visitor.
I opened the door to be met with a doe eyed, dark haired beauty. Stunning wasn’t a word that would adequately describe the vision before me and I must admit my heart skipped a little beat.
“Hi can I help you?”
“Mr Peter?”
Those two brief words revealed a wonderfully sexy accent.
“Yes.”
“I’m Monica. I think you were expecting me.”
I was expecting the new cleaner. I was expecting some frumpy middle-aged woman. Not a high heeled beauty.
“Come in please.”
Monica floated past me. She smelled divine. She walked with confidence and attitude. My cock stirred while the voice in my head tried willing it to go down.
In the living room, she took off her raincoat and slipped off her shoes. She wore jeans which were not too tight but still showed her curves. She had a purple vest top which was cut low enough to show her boobs which were not too big but superbly round. Her pink bra straps were visible. I took a deep breath.
“Hi, I’m Pete” I said outstretching my hand.
Monica giggled slightly. It was endearing. “I know. That’s why I asked your name when I arrived.” She smiled.
God I never believed in love at first sight but I was certainly experiencing lust.
“What would you like me to do?” she asked as she produced a scrunchy and pulled her hair into a ponytail. That merely emphasized her wonderful cheekbones. She wore very little make up which made her natural beauty shine through.
I had so many answers to that but thought better to keep it business.
“What did you do for the previous owner?”
“I started in the bedrooms, did the bathrooms moved into the kitchen and finished off in here.”
“Well, that will work for me. Is there anything you need?”
“As long as your stuff is in the cupboard like Maisie then I can just crack on. It normally takes about 90 minutes.”
“Great. I’ll try and stay out of your way and you just do what you need to do.”
She worked away quietly and diligently although I suspect she caught me staring at her a couple of times. I couldn’t help it. She was really quite gorgeous. When she was done, there was a light sweat over her face and chest. She glowed. I paid her. We agreed Wednesday would be the usual day for her to visit. She put on her coat, gave me the cutest wave and left.
I immediately went to the bedroom, admired her work and had a massive wank over the images I’d stored in my head.
Over the weeks we chatted and I found out more about her. She was 27. She was from Mexico. She’d studied at the university in the town. She did a graduate degree but couldn’t find work when she was done. She asked a friend of a friend if she could fill in when her cleaner left and over the course of about 18 months, she’d built a small company which employed a handful of women.
She was smart and sweet and funny and I found myself looking forward to her weekly visits and the wank that would inevitably follow. In fact, I found it hard to make friends in the town and she was quickly becoming my main source of human contact.
I’d move to the state after I broke up with my fiancé. It kinda made sense to travel to the other side of the country for a fresh start. Not least because my fiancé said she was going to tell all our friends and her family about why we split up.
She’d come home one day – in my defence my earlier than she said she would – to find me standing in front of the mirror of her bedroom in her leather dress and black heels.
I’d been a crossdresser from as early as I could remember. Sister’s clothes growing up. Mom’s as I got older. I’d stopped when Dad died. But the urge was just too strong and I got caught by Mom when I got stuck in her old wedding dress. I knew I was busted. The zip stuck. I couldn’t undo it and at a certain point I realised I was either going to ruin the dress or get even more stuck. Afterwards I thought I should have just broken the zip but I wasn’t actually sure that would help.
All I could do was sit there and wait for her return.
She walked in the house and called my name. I said nothing. I knew she’d made her way to her room eventually. When she walked in the shock on her face was obvious.
“Petey, what have you done?”
I knew my rough make up job had been made even worse by the tears of fear that had tumbled from my eyes over the past thirty minutes. I knew when she was due back. And I knew I’d watched every minute tick down with a growing sense of dread.
I burst into tears again. She walked over and grabbed my head and hugged me.
“Shsshhhh baby. It’s no big deal.”
She let me cry.
“I don’t know what to tell you. I got stuck trying your dress on. I’m so sorry.”
“Petey it’s not a big deal. I know you’ve been trying on my bras and slips. I know you’ve tried my makeup. It’s ok. Let’s see what you’ve done here.”
She stood me up and spun me round. “Are those Stacy’s heels?”
I nodded.
“Look I don’t mind you trying on my stuff. I really don’t but Stacy will be upset if her little brother is rummaging through her drawers. Please tell me that’s the only thing of hers you borrowed.”
I nodded again, not trusting to say anything in case I burst into tears again.
“You’ll kick yourself when I tell you what trapped you. A little corner of ribbon got stuck in the zipper. If…I …just…tug it…”
I felt the fabric ease and the zip slip down with ease.
“Mom, don’t.”
“Petey I want to see what you have underneath.”
“Please don’t.”
She finished unzipping and the dress fell from my shoulders. I turned to face her and I heard he gasp.
“My god, that’s gorgeous. That’s not mine – and you say it’s not Stacy’s…so who does it belong to?”
I stood in front of my mother in a wonderful white silk teddy. The panels were soft and shiny and there was some lovely lacing around the bust. Detachable suspenders were holding up a pair of lace topped white silk stockings which ended in Stacy’s white high heels.
The acute embarrassment was arousing and my cock was starting to stir. I moved my hands over my front only to be pulled away by my mom.
“No, no no. Now is not the time to be bashful. Well? Where did you get the sexy lingerie?”
I dropped my head.
“It’s mine.”
“It’s lovely. Where did you get it?”
“I bought it at the store in town. After Eight. I told the lady it was for my girlfriend but I think she knew it was for me. She said the elasticated waist would pull me in and give me a nice figurer. She threw in the stockings as well.”
We talked for maybe 20 more minutes. She asked me the usual questions.
Was I gay? “No.”
Did I want to transition? “No.”
How long had I been doing it? “Since I was about 4.”
Did anyone else know? “No.”
Did I like girls? “Yes.”
Did I have more clothes of my own? “Some undies and nylons. A little skirt and top, a dress. And an old tennis dress that Stacy asked me to take on the last run to goodwill.”
It felt weird but also really natural to be talking to mom, perched on the end of her bed in lingerie and heels, her wedding dress in a heap on the ground between us.
“You must have been so panicked when the dress got stuck?”
She saw the whole idea moved me close to tears again.
“Look there’s a lot more we need to discuss but I think you should slip out of the lingerie and heels. You said you had a tennis dress. Go slip that on and we’ll go downstairs to finish our conversation. What do I call you?”
“I don’t understand.”
“I’m guessing you have already picked out a name to use when you dress. What is it?”
I swallowed hard and looked at the ground. “Jennifer.”
But that’s…you were …”
I finished the thought “The name you were going to give me because you were convinced, I was going to be a girl.”
“That’s very sweet you would pick that. I’ve always loved the name. Well Miss Jennifer, why don’t you nip off and change and perhaps do something about that” she said pointing at the massive erection I had in my teddy that hadn’t gone down, fueled by the humiliation and embarrassment. “We don’t need you tenting in your dress at the kitchen table.”
I nipped to my room and jerked off. The whole idea of being caught had been so exciting and embarrassing I couldn’t help it, although when I spurted my load, I immediately didn’t want to stay dressed. But rather than upset mom, I found a bra and pantie set in white and threw the tennis dress over my head and went downstairs.
We talked for ages. I felt very comfortable. She asked lots of questions and I think we both came to better understanding of what exactly was happening. It certainly clarified a few things for me about why I dressed. And we came to agreement.
I could dress when I felt the need but I wasn’t to do it in secret anymore. I could take anything she or Stacy threw out, but couldn’t rummage through their drawers and closets any more. Stacy was at college and didn’t need to know. It would be our secret. Mom would buy me shoes and boots. I would have to get a job fund other purchases. I could do odd jobs at home and with our neighbours. I could do yard work, or painting or minor auto repairs (I was good at that) and I could be some cleaning.
Mom insisted my first purchase would be good quality make up and a wig. And she would help me get more proficient than my early feeble efforts which were on display. And I was not to be what she called “a hairy pantie wearer. That, my girl is disgusting.”
Pete could ask permission for Jennifer to visit. And whenever she did, Pete would step away. It was an arrangement which worked for my last two years of high school and first two years of community college. Jennifer was a frequent visitor and mom treated her as she had Stacy.
I then transferred to a state college for the final two years of my degree and Jennifer only made fleeting visits home and certainly never at school.
I built up a good group of friends; boys and girls. I was funny and smart and popular. I was reasonable at sports, but especially good at tennis and swimming. That meant I could keep my body hairless. And in the last months of college, I was told the novel I’d been working on had been signed to a publisher. I was going to be a writer.
At my graduation party in a restaurant near school, I met Ellie. She was blonde and sweet. She had a killer body. She was about my height, so towered above me when she wore her three-inch heels. Which I think she did every day. She was stylish and sexy. She wore expensive labels and knew how to put together an outfit. I’d noticed her months ago but thought she was way out of my league. I loved her clothes but I liked the girl more. That was a first.
We got talking at the restaurant. My mom liked her immediately. I remember Ellie’s laugh. She laughed a lot. At my jokes. And it wasn’t put on or affected. It seems she genuinely liked me.
Others left the party. Mom headed off to her hotel with a wink and a smile. And Ellie and I chatted for ages. Eventually she looked me straight in the eye “So Pete, tell me how many more times do I have to touch your arm before you get the message, I want you to kiss me.”
“Just one.”
That touch was electric, and I leant in and kissed her. Hard but passionately.
Within a month, we’d set up home in an apartment, not far from the University. I was working on my second book, the advance already paid. And she was looking for a job. Although by all accounts, she didn’t have to as her family was very rich. I mean, ‘father only flew private’ sort of rich.
The second book sold well and another publisher wanted me to write a third.
They offered a crazy sum of money as an advance.
Ellie and I grew closer. I liked her family. Ellie clearly got her good looks from her Mom. Her dad was smart and driven but unlike many rich guys I met, wasn’t a jerk.
We got engaged on holiday in Scotland. Ellie loved golf. I proposed on the bridge across the 18th at St Andrew’s Golf Course. Dozens of tourists took pictures and cheered when she said the sweetest words I think I’ve ever heard “Oh my god. Yes, of course I’ll marry you.” I was exceptionally happy.
The wedding was planned for the falling summer and as a Christmas present, her parents bought us a house. I’d made enough money from my books that I could buy us one myself, but her father was insistent.
A month before the wedding I was at home. I’d been scrolling through the internet visiting sites that perhaps had been neglected in my new life, but hadn’t gone away. There were sites for cross dressing clothes and accessories. There were picture sites like Flickr with groups I hadn’t visited in ages. There were fiction story sites. And of course, there were porn sites.
I’d thought about telling Ellie about Jennifer but didn’t think she’d understand. I asked Mom for her advice and she told me that as much as I had shut down the dressing in college, it hadn’t gone away. She said Jennifer’s stuff would remain at her house if I ever needed the release. The call on whether to tell Ellie was mine. And I decided not to ruin a good thing.
That afternoon, I looked at the clock. Ellie wasn’t due back for another thirty minutes. Just long enough to slip into something of hers and have a little fun.
I made my way into the bedroom. I felt the plush carpet under my feet. Her parents had spared no expense giving Ellie what she wanted. I knew what I wanted now.
I went to the drawers and pulled out a bra and panties and a pair of black hold up stockings. I loved Ellie liked hold ups more than stockings and garter belt. Then I opened the huge walk-in wardrobe. I saw it hanging up and felt the cool soft fabric. It was expensive leather. And when she wore it, Ellie looked amazing. I just wanted to steal some of the magic.
I took the leather dress off the hanger and walked to the bed. I pulled off my t shirt, shorts and boxers. I’d always been pretty light on the body hair. The swimming helped. And what little I had matched the blond on my head. I slipped the silky panties on first. Luckily, we were roughly the same size (is there something programmed in cross dressers that they look for partners who are close in body shape?) I eased the smooth silk up over my legs, over my ass and tried tucking my growing cock. Picking up the matching bra I hooked it at the front and spun it around, slipping the delicate straps over my shoulders. I had no time to find something to pad the cups, so tried to create a little bit of boobage with what God gave me.
I eased the stockings up my legs, pulling the hold ups to the top of my thighs.
Then the dress. Oh, the dress. In all it’s delicious, delicate sexiness – there was the dress. I remember when Ellie first wore it. I couldn’t take my eyes off it. See. I said it rather than her. And I knew it was the dress that turned me on more. She looked awesome But I knew at some point, Jennifer would want to try it.
I unzipped it. Checked for any loose threads – you never make that mistake twice. And then slowly stepped into it. It felt gorgeous. The soft fabric – the silky liner. It was exquisite. I pulled it up over my boobs, stuck my hand around the back and managed to zip it up. It looked and felt wonderful.
It came to just over my knees. And if you could ignore the lack of a wig and make up, I’d done not a bad job. I smoothed the dress over my body with a little wiggle and turned to the mirror.
“Well, I have to say Jen, this is perhaps the sexiest dress you have ever worn.”
I looked for some shoes and found some shiny black patent three-inch heels. They were a bit tight but they complemented the outfit. I found a string of pearls and a little black bracelet to set it all off. It looked quite presentable. I walked from room to room, soaking in the feeling of the dress against my skin, the bra against my chest and the panties slowly rubbing on my cock. I went back to the room and stood there looking at the reflection in the mirror and trying to decide if I would wank dressed or put everything away and jump Ellie as soon as she came home. In the end I had neither option.
“What the fuck Peter?”
Ellie was red with anger. She was standing in front of me, jeans, light jacket white t shirt and three-inch yellow heels.
“What the fuck is this? That’s my new dress. My heels. My god you have boobs. You have my bra on. This is a fucking nightmare.”
“Hold on a second. I know you’re upset. ”
“Upset. You’re fucking right I’m upset. One month to our wedding and I find you in our room in my clothes. Yea, I’m a little bit upset. What the fuck do you think you’re doing?”
She dropped the bags and walked straight in front of me and pulled up the dress. It was tight and that wasn’t easy.
“My fucking stockings and my panties. You fucking pervert. What the actual fuck are you doing?”
“Look, let’s just calm down.”
Rookie mistake. Never in the history of marital arguments has anyone ever calmed down after being told to calm down.
“Calm down. Calm. Down. You are fucking dressed to the nines in my clothes and you want me to calm down. Is that an erection? Are you actually getting hard? This is turning you on. Fuck. I need to get out of here.”
She turned and strode out of the room and down the stairs. I went to the hallway “Stop. Ellie. Please. Let me explain.”
“Fuck off” she spat and she slammed the door. I heard her jump into the car and tear off down the driveway.
I could hardly run after her dressed as i was and I knew I I had seriously fucked things up.
I went back to the room, slipped off the heels, rolled off the stockings, eased off the dress and removed the undies. My cock was raging. And despite myself, I tugged myself to a conclusion. The humilation again a huge driver.
But I knew I was screwed.
I didn’t sleep. Ellie didn’t come home. I was beginning to get worried when I heard her car.
She was wearing the same clothes as yesterday. I met her at the door.
“Thank god you’re ok. I was worried.”
“Pete. We’re done. It’s over. I’ve cancelled the wedding, I loved you. I thought you loved me. But I see this massive secret you’ve kept from me and I don’t know who you are.”
“Please let me explain.”
“No. My mind’s made up. I want you packed and out by the end of the day. Take the clothes you wore. The heels too. Even the undies. I’d feel sick if I ever saw them again. You’ve hurt me. To my very soul. And go. Away from here. Far away from here. ”
I started to cry. “Ellie we’re good together. I can explain this. Please don’t throw it away over a misunderstanding.”
“I could never trust you again. Look I don’t want to get into name calling but I can’t be married to a fucking sissy. I can’t lie there with you wondering if you’d rather have a cock up your ass. I can’t buy clothes wondering if you’re going to sneak around trying them on. I spoke to my parents. It’s over. Take the car, take anything you want from inside the house and go. If you’re not out of the house by the end of the day, Dad is going to get his attorney to cripple you financially and I will tell everyone we know why we’re splitting up. Jesus Christ. What must your mother think of you? I bet you wore her clothes growing up. It makes me sick. Nope we’re done. It’s done. Go.”
She turned back to her car and drove off. I’m not sure she even looked back. I knew I was in tears and my heart was broken. I was convinced we’d sort it out. But the first night without contact stretched to a week, then a month. I called her parents but they hung up. I called Ellie but my number was obviously blocked. I think it’s rare when a woman makes up her mind in these situations to ever change. So, I spent some time with Mom and then decided to head across the country. A new place. A new start. And, as I was to discover, Monica.