tagTransgender & CrossdressersThe Handyman is a Real Handy Woman

The Handyman is a Real Handy Woman


"How does it look?"

My girlfriend spun around, asking how I felt about her new dress. I hadn't gotten this far in our relationship by always telling the truth.

"It looks great babe."

I could see the reflection of Bridget's frowning face in the mirror. "You don't think it makes my ass look big?"

I wish it had. What man truthfully prefers a small ass? I never understood this preoccupation women had from my generation with being at their skinniest possible weight; the kind of skinny where bones stick out of their skin. I, for one, prefer looking at a girl with a big pair of knockers and a nice fat ass. Don't get me wrong. I'm not lusting over the women from My 600-lb Life, I just want something to grab onto.

*Snap Snap* "Did you hear me?"

"Oh, yes... sorry, I did. Your butt looks good, babe."

"I can't even hold your attention for five damn minutes, Julian. Where's your head at?"

"I don't know babe. I was going over the things I have to do today."

Bridget pulled out her work clothes, "That shouldn't be a long mental list. Play around on the computer all day while your girlfriend goes to work."

"It is a bit longer than that..."

Bridget walked into the bathroom and pulled the cap off the mouthwash, "Don't forget the apartment's handyman will be here around noon to fix the fridge," she took a long swig of mouthwash and then sputtered out, "Let him in and make sure he doesn't steal anything."

"Oh okay. I'll add that to the list."

She slipped her new dress off and got her skirt and blouse on. "And if jerking off into the robe my mom sent me is on that list of yours, cross it off now."

I moved closer to Bridget now, pulling her against me, "I already apologized for that."

"I'm fucking serious, Julian. If I find one more cum stain you're going to regret it."

Bridget's lips thinly pursed and I covered them with mine, "You know, I wouldn't have to do so much jerking off if you'd..."

"Don't bring this up now. Fuck, Julian! With everything going on at work, I don't need you whining at me."

"Okay, okay. You're right. I'm sorry."

Bridget grabbed her purse and shot straight for the door. I loafed into the kitchen and thought I'd make myself some breakfast. Pulling open the refrigerator door, I smelled spoiled milk. Damn it. Noon couldn't come fast enough.

For the next few hours, I knocked out some work on my laptop. Contrary to what Bridget thought, I didn't just play around all day while she worked. After feeling particularly productive I pulled up one of my favorite websites. A buxom lady appeared on the screen and warned visitors under the age of 18 to close the webpage.

I clicked through that page and was greeted by dozens of pictures of the the most beautiful, big-breasted women in the world. I took my dick out and started a video.

I was getting close to cumming just when there came a knock at the door. Quickly closing the video and fixing my clothing, I tried to ignore my hard-on and opened the door.

"Hello, I'm Naudia." A hand reached out to shake mine, "I'm here for the fridge, right?"

The handyman was a woman. My eyes took in her shape; a beautiful woman! Her hands were soft, but her handshake was firm. "Julian." I spoke dumbly.

Naudia was around my height and instantly reminded me of the some of those woman I had been looking at online. The only exception being that she was much more beautiful. This lady was gorgeous!

"I'll have a look at it." She pulled her hand out of my grip and giggled.

Lugging a box of tools in her other hand, she walked ahead of me to the kitchen. Her pear-shaped ass captivated me. She snapped her hips back and forth on the way there in a pair of well-worn jeans that looked almost painted on.

Naudia got into the kitchen and asked if she could look inside the fridge. I nodded my head and warned her about the smell of the spoiled food.

"I'm sure I've smelled worse. I'm not so dainty." She giggled again.

I lifted myself up on the counter and watched Naudia poke around for a minute. My eyes stuck to her ass like a heat-seeking missile. Bridget asked me to watch the handyman and I was going to take that very literally.

"I'm gonna take a look at the cord. Want to give me a hand in moving it?"

"Sure." I hopped off the fridge and waited for her instructions.

"Alright, just grab it on the side and slide it with me when I say; let's put those muscles to work."

Naudia squared her body up with the fridge and then gave me the word. We huffed and puffed until the giant appliance finally moved.

"Good work." Naudia's full lips opened into a smile, "Let me just take a look."

She bent down to inspect the cord and I got in a good look as well. The material of her pants rid up the crack of her ass even further. My cock started to swell. I nervously readjusted myself.

"Everything's alright back here. Hmm... maybe it could be--yeah, I better check that." Naudia opened a panel in the fridge and tinkered around.

"Alright, that's it. You need a new component here," Naudia pointed, "I'll have to get one and bring it back. Will you be here tomorrow?"

"Umm.. yes." I answered

"Are you okay?" Naudia smirked and I could have sworn her eyes flashed down to my crotch and then back up at my face.

"Yeah. I'll see you tomorrow. Thank you for coming by."

"Mhm, I know I'll see you or wife."

"I'm not married," I said with a puzzled face.

"You live with a woman here, don't you? Two names are on the lease."

Oh yeah, Bridget. Duh. "Yeah, Bridget. She's my girlfriend. She works during the day."

Naudia gave me a funny look, "I don't think I'd leave you alone all day if I were her. There are a lot of desirable women around here. Plenty would be willing to jump into bed with you, I'm sure. Especially if you're as virile as you look." Her eyes flickered back to my crotch again.

My face turned ten shades of red, "I doubt she'd worry about that with her busy schedule."

"I think you make time for the things you want. It was nice meeting you, Julian."

We shook hands one more time before she left. I opened the door for her and we waved goodbye. Until tomorrow that is, and tomorrow couldn't come soo enough. My eyes followed the seductive sway of her hips once again before I shut the door and exhaled deeply. Jumping on the couch, I pulled my cock out. I pumped out two loads and I thought about Naudia while doing it.

Bridget got back a few hours later and checked the fridge first thing. "It's still broken." Her voice seemed more whiny than I remembered it.

"She'll be back with the part it needs tomorrow."

"She?" Bridget shot me a questioning glare.

"Yes, she."

"A female handyman? A Handywoman! That's a strange occupation for a woman." Bridget thought for a moment, "Is she pretty?"

"Not as pretty as you, honey." I lied.

Bridget rifled through the cabinets and couldn't find anything to eat. "I just got home from work and there's nothing in this house to eat. Why didn't you go shopping? I'm starving!"

"I'm sorry. I'll go out and get you something, babe."

Bridget sighed, taking a seat on the couch in the living room. "Forget it. I just remembered I threw up at lunch. I don't want to ruin my diet on fast food. Even you should know that." She made an ugly face at me.

We squabbled here and there over the rest of the night before going to bed. Bridget rejected advances and rolled over, falling asleep. I couldn't fall asleep and you better believe I was going over the time I spent with Naudia and those looks she gave my crotch.

The next morning passed quickly. I spent most of it on the laptop. Cleaning up a little bit after Bridget left for work, I put on some nice clothes.

I answered the door on the first knock and was greeted by Naudia's sweet smile and what seemed to be a fresh coat of lipstick.

"Good afternoon, Julian. How are you doing today?" Naudia walked to the kitchen and set out her tools. She was wearing shorts today. Her legs looked impossibly smooth.

"I'm good, thank you. How about you?"

"Pretty good. I didn't get much sleep last night." She cracked her neck, "I'm glad to see you today. I meet a lot of... unsavory people."

Naudia got to work on the fridge while we talked. I watched her work intently. The sway of her body and the way her breasts danced around in her shirt made every single action interesting.

"So long how long ago did your girlfriend leave?"

"A couple hours ago, I'd say."

"And she leaves you all day?" I nodded yes, "You poor lonely soul. I hope I'm not gonna be your only company, that'd be a shame."

I laughed, "That's in no way a shame. Honestly, seeing you yesterday was the highlight of my day."

"You really mean that?"

"I wouldn't say it if I didn't."

"You're a real sweetheart. This girlfriend of yours better keep you close before someone else snatches you up."

"Yeah well... Bridget doesn't exactly do that, but thank you."

Naudia's face softened, "You mean you two, you aren't...?"

"No, no we're not. She comes home in a bad mood and it pretty much stays that way."

The conversation shifted, "Can you hand me a wrench?" She asked.

I looked through her box of tools and handed her the wrench. Naudia flashed me a smile and before long she stood up.

"I'm done. It should work now. It'll take a little while to cool down again. Get rid of this spoiled food and you'll be back in business."

"Oh great. You've been wonderful."

Naudia put her tools away and then stopped in her tracks.

"Is something wrong?" I asked, concerned.

She gave me a sad look, "She's not even going to be appreciative, is she? Your girlfriend, I mean."

"I doubt it."

"Screw her then." Naudia looked around for a moment and then back at me, "I have some time now before my next job. Want to do something exciting?"

"Uhh... like what?"

"Well, you've been checking me out for the past two days. You know what would really piss your girlfriend off, if we screwed in her bed."

I nearly fainted. "What... are you serious?"

"Give me a chance and I'll rock your world, mister."

We both laughed and then just like that she was in my arms, our lips pressed together. Her full, soft lips were a revelation after spending so long only kissing Bridget's thin ones. Naudia's tongue slipped into my mouth and played tag with mine.

Naudia pulled her lips off mine and I struggled for breath. She spoke first, "There's something I have to get off my chest first."

"Please let it be your shirt."

She giggled, "No. Well, really, it's just a formality," Naudia bright brown eyes looked into mine, "Umm..." She stammered.

"What is it?" I lifted her hands up and kissed each of them.

"I'm not your average girl, Julian."

My hands slid down over the swell of her ass, "My average girl doesn't even pay attention to me. She yells at me and probably fucks her boss."

"I have a penis, Julian."

"Oh shit." I muttered. I mean oh shit. "You have a dick? ...What the fuck?"

"Julian, if that's a deal-breaker, I understand. I'm not going to apologize about it. I do have a dick. I love having a dick. It's as dear to me as yours is to you. If you can't handle that, I can be out of here in two seconds."

I thought for a moment. Okay, she has a dick. But, I'm no homophobe. This vibrant, beautiful woman had stepped into my life and she could step out just as easily if I said the wrong thing.

"No, don't go. I can handle this. It's not a deal-breaker. You're just as gorgeous now as you were a minute ago."

Naudia's lips collapsed on mine and she sucked my tongue into my mouth. "I knew you'd say that. I just knew it. You're the one I've been looking for."

The space between our bodies disappeared. Her big breasts thrust against my chest. My hands returned to her butt and I gave it a rough squeeze.

"How about we take this to the bedroom." I tried to say as sexily as possible.

"You've got it." Naudia jumped into my arms. I lifted her up and carried her to the bedroom Bridget and I shared while she covered my neck in kisses.

By the time we made it to the bed, Naudia had my shirt halfway off. She mewed like a cat, working the buckle of my belt open. I pressed my face between her shirt-covered tits.

"I think I've see you in pants long enough." Naudia said while she slipped them down my legs.

A minute later all but our underwear was on the floor in a pile. I felt her cock lodge between my thighs as we frantically kissed and continued to scratch at the few articles of clothing we still had on.

Naudia slid her frilly panties down her long legs and I saw her cock for the first time. To tell you the truth, I was expecting a little pink cock. Instead, my eyes bugged out as I saw a thick, veiny, whale of a cock--even bigger than my own.

"She likes you, Julian. Just look at how big she got."

"I can see..." I said, a little dumbfounded.

I looked up and Naudia had pulled her bra off. Her soft, round tits and hard nipples made my mouth water. I kissed up her stomach, pulling my boxers down as I did it. Our dicks instantly linked together. She laughed as I excitedly mauled each of her tits with my mouth.

"And it looks like your boy down there likes what he sees, too. Mmm... that's good." Naudia's hands massaged across my back as I loudly sucked on her nipples.

"Those your girlfriend's?"

I followed the trail of Naudia's eyes and saw a pair of Bridget's panties hanging off the knob of her nightstand.

Her nipple fell from my lips, "Yeah."

A mischievous grin played across her face. She leaned over and grabbed Bridget's panties.

"Is this a child size? I didn't know sizes even got this small." She giggled.

Naudia edged off the bed and I started to get a little frustrated, my dick aching against the mattress. She slipped the little pair of panties up her legs and they stopped midway up her thighs, unable to go any farther without snapping.

The eroticism of the moment took over complete control of my brain. My girlfriend's underwear were on Naudia and they couldn't even get past her curvy thighs. Meanwhile, Naudia's rock-hard cock bobbed up in the air. I fell to my elbows on the bed and engulfed Naudia's reddish purple cock head into my mouth. She groaned, her hands immediately covering my head.

Sucking my first cock felt as natural as anything I'd ever done. Naudia's spongy, hard cock slid deeper into the warmth of my mouth. Her cock twitched and it sent tremors throughout my body. I could feel every movement of Naudia's body; every intake of breath; every jab of her hips.

"Oh fuck, Julian, you're more adventurous than I thought."

I smiled around her cock, sucking deeply and running my tongue over the sides of her shaft. Her dick tensed and Naudia inhaled sharply. My hands ran up her smooth thighs and teased her low-hanging balls.

"I'm so charged. About to cum. I hope you don't mind swallowing." Naudia spoke slowly, pausing in between each sentence.

Naudia's hands held my head more harshly. She thrust her cock deeper into my mouth than it had been before and then shouted, hot liquid suddenly spewing from her cock. I swallowed hard as several mouthfuls of sticky cum spilled down my throat.

"Mmm... I love a man who can clean up his own messes." Naudia slowly wrenched her shrinking cock from my mouth while I licked up the last bits of cum from her shaft and balls.

I licked the sticky discharge from my lips, "How'd I do?"

Naudia arms wrapped around my back, her lips crushed against mine and her tongue ran in circles through my mouth. We embraced for a long moment, my hands kneading and spreading the bare flesh of her big butt.

"That was fantastic! I think my girl loves you forever after that. And you've never done that before?" She smiled.

"Nope. Never done that before."

Naudia's hand grabbed a strong hold on my cock; her hand stroked up my shaft. I was going to explode any minute--all this excitement had already gotten to me.

"A girl should clean up her messes too. I can tell your boy is about to blow. I'm sure he'd rather do that inside my mouth than out of it."

I laid back on the bed and Naudia responded by kissing her way down to my crotch. She licked my lower stomach and then down my thighs. Naudia ended up between my legs when her hand resumed its stroking of my cock. Then her lips opened and she nipped at the head of my cock.

Her lips encircled my cock head and I felt her start to suck hard on the tip while her hand squeezed and stroked my shaft. Naudia nursed on the tip before pulling more of my dick into her mouth. Pretty soon more of my cock was in her mouth than out of it. The sound of sucking that ensued cut through the air. I moaned under my breath and wrapped her hair up in my hands.

"I'm gonna cum, Naudia. This "mess" is all yours." Our eyes met in that immensely pleasurable--almost painful moment when your cock gives a powerful jerk as it orgasms and your piss hole doesn't feel big enough to release the load you're about to shoot.

Naudia kept sucking away on my cock, barely batting an eye when my dick started spurting. I could feel her throat closing in around me as she swallowed. I kept cumming, holding her beautiful head in my hands and giving up every ounce of cum my balls had.

We were both sweating and red-faced by the time it was over. Naudia gave my cock head a dozen kisses and then pulled her body up to lie down next to me. I felt her dick press into my thigh. It was hard again!

"That was your first time when you blew me, Julian. You're still an amateur cocksucker. You have a lot of passion though--and a lot of natural assets to start with," Naudia chuckled, her finger tracing along my lips, "I have a bit more experience in the art of cock-sucking. You could be a pro, though, if we practice together."

I covered her lips with mine and tasted my own cum; which didn't bother me at all. "I want to get better if you'll help me." I grinned. "We don't have to stop yet. Bridget won't be home for hours. And I think your "girl" is even harder than before." My hand slid between our bodies and grasped her erection.

"Don't worry, big boy. I wasn't planning on going anywhere," Her lips planted on mine. "I was actually thinking we might try something else--if you're up for it."


"Hmm," Naudia's hand rubbed across my hip, "How do you feel about... anal?"

"Great! Let's get started," I grabbed a handful of her ass.

Naudia's laugh filled the room, "Excuse me, mister, but..." Her hand pulled on my cock, "You're still a little limp. It's my turn."

I gulped. Before today, I'd never considered being fucked in the ass. What straight man had? Well after everything that happened today, I wasn't so sure that I was straight. Those questions could wait until another day. For now, I had the woman I wanted in my bed and I was going to keep her there; that I knew.

"I'm game if you are. What... what exactly does this entail?"

Naudia seemed to read the uncertainty on my face, "It's gonna be okay. We'll take it slow and I won't hurt you, okay?"

"Okay." My hand caressed her tits.

"Turn over and we'll get started."

With a little apprehension, I turned away from Naudia. The next thing I heard was Bridget's nightstand drawer opening.

"I hope your girlfriend doesn't mind that we're borrowing a little bit of lube. It's going toward a good cause!"

Listening to Naudia lube up her cock felt a little cold and impersonal, but then I felt Naudia's warm breath on the back of my neck. Her leg hooked over mine; she started places butterfly kisses on my neck. I feel her nipples dig into my back and then the slippery head of her cock brush against my ass.

"Such a cute little ass. My girl is one lucky bitch today."

Her slippery cock poked between my cheeks and pressed against the entrance to my asshole. I tensed up, my teeth gritting and my back arching.

Report Story

bySugarandSalt© 21 comments/ 152991 views/ 234 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: