Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress the entire time except for when I have to go to the office. Lucky me, most times I work from home.
Sunday, my first day alone, I take a long bath and finally remove all that unwanted hair except for a small strip about my clitty. After the bath I rub lotion all over my clean body and walk over to the mirror to really see what I look like. I tuck my clitty between my legs and look up. Months of hard working out in the gym finally gave me a flat tummy and the girly look I had been looking for. I turn side ways and take a peek, I even have a great looking ass. If only I can get the nerve to go out dressed, hiding at home dressed when nobody is at the house has gotten old.
I managed a few times to get all dollied up and drive around. Even one time I drove to a town close by and attempted to go in a friendly bar that catered to all kinds, and lost my nerve. I told myself this time it would be different.
I head up to my hiding place for all my fem items. Over the years I've ended up with 2 trunks worth of fem attire hidden in the attic. I move my collection to my bedroom closet and put away all my things. I locate my favorite lavender camisole and matching thong with pretty flowers on it and slip them on. Oh what type of finger and toe nail polish first? I pick out a coral pink neon color. While waiting for the polish to dry between coats, I go to a few of my favorite websites to see what new clothes, shoes and accessories I can order. I find a real nice party dress with ¾ lace sleeves, scalloped tiers of lace with beading, you can never go wrong with a little black dress. The shoe site has these cute black pumps with 4” heels and rhinestone criss cross straps. I place my orders, they should be here by Friday. I can’t wait!
The week drags by, the only benefit I don’t need to go the office, and this gives me a chance to work on my makeup skills. By Thursday morning I finally get the look I have been looking for. My eyes have a nice smokey look and after blending the foundation colors correctly, the makeup, blush and lip stick looks great.
Friday morning and I start my regular routine, check for unwanted hair, a little waxing if needed, quick shower then rub moisturizer on my body. I slip on my bra with C cup forms, pull up my thong gaff and tuck my clitty away. Quick makeup job, bob wig, pair of black short shorts, violet sleeveless shirt that I tie the bottom of the shirt in a knot, and a pair of sandals. I sit down at my work station and start plugging away at today’s assignments. I become so accustomed to be dressed that I don’t think off it any more. Morning goes by fast, after lunch I am almost finished up for the day when the door bells rings. Not thinking I go to answer the door.
Before I realize the door is open I am looking at my mail lady, Emily. She is holding two packages that require my signature. (My mind is racing…..does she recognize me? How should I sign? Use my fem name Deedra or Dan?). Emily looks at me and has a big smile on her face.
Emily says, "Hi, Dan, you look really cute. I need you signature for these packages why don’t we step inside so you can get a pen?"
I turn away and walk back to my work station.
She says, "Boy that's a nice ass you have in those shorts."
I almost stop in my tracks, my face in turning bright red. I pick up my pen, turn around and Emily is right in front of me and the front door is closed!
She says, "I need Dan’s signature on these two packages, but you don’t look like Dan today. What name should I call you when you are dressed?"
I have a confused look on my face and am speechless!
Emily says, "I have been delivering packages here that come from companies that I know sell to crossdressers. I have suspected that you have been dressing for years. I know your wife is away and I finished my route early today and drove over in my car to see if I was right. So what shall I call you?"
I can barely talk and manage to say, "Deedra."
"Ooh I like that name."
"Are you going to tell my wife?"
Emily says, "No silly, you are so sexy, I was hoping that you were a cross dresser."
"Are you going to keep my secret?"
"Only if you do a few things for me," she says.
"What is that?"
"You have to make love to me."
Emily kicks off her shoes, unbuckles her pants and they drop to the floor. Then she unbuttons her shirt and drops that to the floor. She pulls a hair band out and flicks her head, lets her brunette hair fall down past her shoulders. Standing in front of me is a petite woman about 5’ 4” with cute red shelf bra and matching panties. "Well what do you think?" she says.
"You are so hot, but I don’t understand with that body why would you want me….you could have anybody."
"Not all guys can handle a girl like me and you are so cute silly girl." Emily slides her panties down and out pops nice little cock.
"Wow that looks fantastic, you look so beautiful. Are you sure you want me?"
"Get on you knees and suck my cock and you’ll understand!" she says.
I kneel down and start to stroke her cock, then reach down to cup her small balls and find that she also has a pussy. I look up into her eyes and understand. I lick just the head of her cock and it grows hard. Now it's time to tease her cock…. I run my finger nails up one side down to other side as it starts to twitch. I slip her cock into my mouth, turn my head so my tongue's on one side of her cock and go down on her cock. I pull my head up slowly and stop just before the tip pop out of my mouth… then I rotate my head to the other side of her cock and repeat the process.
I add a tongue swish at the top stroke before turning my head back to work the other side. Emily's moaning. After about 20 strokes…I stop the slow rotation method and start to bob up and down going down to her base and all the way up to tip of the head, making sure to suck really hard when on at the top the head only and then back down again.
I do this over and over again. After a few minutes of this I can tell that she is getting really hot, I can even taste some pre cum.
"Oh Baby," Emily says, "we need to stop and get somewhere more comfortable! My knees are ready to collapse."
I get up off my knees…. she grabs my hand and whispers in my ear, "Where did you learn to suck cock like that!"
"First you didn’t let me finish you off. I always love the taste of cum, there’s not one cock or cum that tastes the same. When I was a teenager and started to cross dress some of my high school friends found out and told some of the other boys on the track team. They made me dress for them and suck them all off for the last years of high school. After a while I started to love the taste of cum and could tell the difference of which cock was is my mouth. Then when I went off to college I met my wife and put off the crossdressing and put the cocksucking aside. I haven’t done this since high school, but you never forget how to suck cock to the brink of explosion, and not letting them cum was one of my specialties."
"How does my cock rate?" she asks.
"It’s first class! Just the right size to get all my tricks to work. My I ask a few person questions if you don’t mind."
Emily says, "Ok."
"Would you tell me about how you ended up with both sexes?"
"That’s for another time… I need you now, let's go to your bedroom."
We walk up the stairs to my bedroom….anticipation has me floating up the stairs as my ass sways back and forth. Hoping that Emily might break my virgin ass. As I open the door Emily grabs my ass then pushes me on the bed. She lands on top of me and we start to kiss. She slips her tongue into my mouth and has my clitty busting to get out. We both stop for air and she pulls my shorts off.
"My…. what a nice job," she says. "Your skin is so smooth, I like the floral gaff thong…let's see what’s hiding under these?"
She pulls my thong down and out flops my clitty.
"Let’s see how much this grows," she says. She starts to blow her HOT breath on my clitty and it comes to life and grows to its full size. "Wow looks like a good 9” cock….boy I can have a lot a fun with this."
I grab Emily and we flop around on the bed and start to kiss again. After a few minutes I reach and remove her bra and start to rub her nipples. This hits one of her hot spots and she starts to wiggle with ecstasy. I can tell that she's ready for the next step. I break away and start to go down on her again.
"No, Deedra, let's do 69. I need to suck your clitty. I want to be on top."
I lay down and Emily brings her prize to me… oh my what to do first? I lick the top of her cock and slide down to her pussy, spend a little time on her clit then slip further down to her ass hole and give her a rim job. I can tell that Emily is enjoying this because she is going down on my clitty and she stops for a minute, grabs the lube off the dresser and lubes my ass. She slowly slides one finger in me. Then she starts sucking hungrily on my clitty again. We work each other over for what seams to be an eternity.
Emily says, "Oh baby…..I’m so close. Can you finger my pussy while you are sucking my cock?"
I start to bob up and down on her cock and at the same time on the up stroke run my tongue around the tip of her cock while my hand works her clit. Her pussy juices start to flow down my fingers. I slide my hand down to her ass, slip one of my moist fingers into her hole. Her cock is now pulsating in my mouth. Emily starts going even faster on my clitty and she has worked up to 3 fingers in my ass now, working them hard. I am ready to explode and can tell she is ready too. I slide my hand back up and start working her clit again, rubbing it between my thumb and index finger.
"Oh baby," Emily says, "Don’t stop I ready to cum!"
She starts to shudder. I feel her cum shooting up her cock into my mouth. Oh my it’s so sweet, not too thick and a full month full. I swallow it down. At the same time her pussy floods my fingers and the taste of cum in my mouth makes me explode. She then licks up my cum and puts my clitty back in her mouth. We both suck each other dry. Emily snuggles up to me and rubs my body.
"I haven’t cum both ways for years, you're fantastic," she says.
We rest for about an hour as we caress each other bodies, then both of us get dressed.
Emily says, "I still need Deedra to sign for the packages…by the way what’s in the packages?"
"A little black dress and new pair of shoes. I was planning on going over to Elsie club in Flairsville tonight. I hear they are friendly to all types."
"Have you been out dressed before?"
"No," I said. "I have driven over there before but have been afraid to get out to the car and go in. I don’t think I can pass for a girl and would get picked on."
"Oh Baby I will pick you up at 9 O’clock and we will go together. You will pass for a t-girl without a problem." She kisses me again. "I have a lot of friends at Elsie."
My head is spinning as Emily is walking out the door. Maybe my fantasy of Emily breaking my virgin pussy with her cock will come true tonight.
To be continued....
(This is my first story, please be gentle with your comments.)
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<a href="https://www.lushstories.com/stories/crossdressing/the-change-up.aspx">The Change Up</a>