Stretching Out [M]y Housekeeper[F]

Flashback to my mid-20s, I’d settled into my first “real job”, and I was finding my way. In decent shape, tall, and well-hung, I’d made a decision to stay single and have fun.

Kelly had been cleaning my apartment for two years. Maybe 34, she was a tiny thing, cute, about 5’2″, red hair, slim, from one of the country towns in the area, but she would often talk about her past working with musicians in Los Angeles and Las Vegas. She’d partied and had a couple of interesting tattoos to show for it, but now she’d calmed down, was close to her family, and did some art on the side. I always liked hiring her because she did a good job, had a good attitude, and showed up on time, and we’d gotten to be chatty about life. Once, when she had a sick pet at the vet, I slipped her an extra $50. That was the only time she’d hugged me, told me I was “amazing”. Beyond that, I didn’t give it much thought.

This day, though, I had to head in to my company’s home office, a two-hour trip, and I decided this was a good a time as any to schedule our next appointment. Once we worked it out, I checked my Facebook, and noticed that she was actually at one of her art shows, hoping to win a raffle for a voucher for a free massage.

I wondered how it was going for her, and texted her again. “How are you doing, anyway? Selling anything?”

“I’m OK. It hasn’t really gotten started yet.”

“At least the weather is great, though, and you’re going to win that massage.”

“I am! I need it so badly.”

“If you don’t, let me know, I give a hell of a massage.”

As soon as I hit SEND, my heart sank. Why did I even say that? I thought I was now the guy who was going to have to find a new housekeeper because I had turned into a creep. After a few minutes had passed, I decided to try to make it right. “That was messed up. I was bored and trying to be funny and it came out badly.”

Another moment passed. “You’re cool. I’m bored, too. Go for it.”

Shit. “Oh. You’ve seen the massage lotion I keep in my medicine cabinet?”

“Yeah. Are you going to make me undress for you?”

Shit. “Will I have to make you?”

“Maybe. I like doing what you tell me. I saw you looking at me last time, when I was on my knees in your kitchen. I wondered what that was about.”

SHIT. “Are any of your other clients cool enough to throw in a full-body massage?”

“No, but the teenagers at that jerk house I told you about with the angry rich lady? Offered me $300 to clean in my panties.”

“Did you?”

“NO!”

“I mean, three hundred bucks is three hundred bucks.”

“They’re horrible teenagers, and it’s not about the money.”

“I’m not a teenager. Clean in your panties for me for free?”

“We could talk about it.”

“You’d probably be surprised at some of the things I like.”

“I was in love with a woman once. You can’t shock me. Try.”

“Wow, so you’re threeway material?”

“I liked it better with two guys, though. Look, what the fuck is this? You always seem so straight-edge.”

“Ask me how I screwed my English professor, sometime.”

“LOL. WHAT?”

We went on like that for the entire train ride. She thanked me for making the time fly by at her art show, I went to my hotel and stepped into the shower to jerk off frantically. After I came, I wondered again. This was probably a mistake, right?

A few days passed without communicating, and we left it alone. When she came to the apartment to clean, nothing was said. Literally, nothing. We greeted each other, then she cleaned without saying a word. As she scrubbed my kitchen sink, I walked in to get a tin of coffee out of the cupboard over her head. Standing behind her, I could see how tense she was, and when I had what I wanted, I put my hand on her shoulder. She jumped and dropped the sponge and some silverware. “Kelly, are we alright?”

“Yeah, we’re fine.”

I left her to her work, and this time, after I paid her, I gave her a hug. She hugged me back, hard. On her way down the hallway, she looked back and smiled at me, then quickly turned away.

A few minutes later, I saw her cross the parking lot, get in her car, and my phone chirped. I had a text message: “I’m sorry. I’m shy.”

“I don’t blame you. Are you sure things are OK?”

“Yes. I want to fuck you. I just don’t know when.”

We stayed in touch from then on, sharing some stories from our past and details of our fantasies. The next time she was scheduled to clean, I checked in on her when I woke up.

“You know nothing has to happen. Everything we said is in fun and you’re good at the work you do here, I don’t want you upset.”

“It does have to happen. I really want you.”

So again, she arrived, tense, silent, and this time I made a move. When she was at the sink, wearing cute little jean shorts, I put my hands around her waist and felt her start to shiver. She kept scrubbing. I leaned down and kissed her ear. Her hand stopped, her head tilted to expose her neck, and I ran my tongue behind her ear. She sighed. “I need to finish your work first.”

The smell of a new woman and the feeling of her tense body made me painfully hard. “It’ll wait. Nothing about it that can’t wait.”

She rinsed her hands under the running water and turned around, pushing her hands against my chest, frustrated. “I need to go to have a cigarette.”

“You told me you quit that.”

“Yeah, well, I need one right now.”

When she returned, she charged through the door and headed right for me. “I texted my friend. I didn’t know what to do. She said to stop talking about fucking you and just fuck you and get it over with.”

She put her arms around me. I kissed her deeply. I could feel she was already bringing her hips forward to meet me, and I slid my hand down her back and over her ass. She tensed up at my touch, then melted. I pulled her shirt off over her head, and led her to the couch in her shorts and bra. We made out like that for a long time, tongues mingling, until she reached down and started feeling for my belt.

When she unzipped and pulled out my cock, I leaned back. She weighed it in her tiny hands, then bent down to take me into her mouth. She was on her knees on my couch, ass in the air, head in my lap, struggling to get me all the way into her mouth and slurping hungrily, and I was done wondering whether this was a good idea or not. “Go get a condom out of my nightstand, now.”

She hurried into my bedroom, knowing exactly where they were, the box of Magnum XLs in the gold foil she’d cleaned past a hundred times. When she returned, her hands were a little shaky and she was having trouble getting the wrapper open, but she managed, then wriggled out of her shorts and pushed me down on the couch. As soon as she slid down on top of me, I realized how vocal she was. She was so tight, tiny, and seemed feral for dick. She held on to the armrest of my couch behind my head and pumped away furiously, nearly in tears with enthusiasm. I made a point of lasting for her, licking and sucking her nipples, and when I could tell she was getting worn out, I grabbed her body and pushed her upright over my shaft, pumping my hips violently into the air, deep inside her and bottoming out. She tilted her head and arched her back, moaning and whimpering, grabbing at my arms but unable to get a good grip the way I had her balanced. “You… FUCK. FUCK.”

After a few minutes of this, she seemed almost spent, so I sat up and put my arms around her. My apartment didn’t have the best air conditioning, and she was dripping with sweat. I pushed her back and carefully leaned forward with her, managing to get her on her back without pulling out. I was pleased with myself for that little trick and smiled down at her. She looked up at me, in the eyes, and smiled back, and I started thrusting slowly, with her hands on my waist. “Are you getting what you need?”

She nodded slowly, breathing heavily.

“Have you ever cleaned for anybody who fucked you like this?”

She shook her head, and I could feel her fingernails grazing my back. “No. Never. I don’t do that, but I haven’t… Had… I need this right now. I NEED THIS OHGOD.”

I ground into her deeply, and soon, I came with her. Her nails digging into my back and ass hurt, and I knew they would leave marks. I was glad it was Monday and hoped the girl I was seeing on the weekends wouldn’t notice. We rested there for a moment, me on top of her, arms and legs wrapped around me. When I finally pulled out of her, she grabbed the condom and tossed it out for me, then brought me a warm washcloth and cleaned me up before jumping into the shower. It was a little odd to have a “first time” with a woman who already knew her way around my apartment so well, and stranger still for her to take the trash out with her when she left. As she left, I kissed her again, and she smiled and walked away happy, though a little wobbly.

I went back to my desk and watched out the window as she got in her car. My phone chirped. “That was perfect,” she’d written. “I have to sit here for a few minutes and stop shaking before I can drive. Can I go on that ride again?”

“Later. You drained me.”

The next morning, I suggested we pick a night for her to sleep over. “I’d love that,” she replied.

Friday night rolled around quickly. When she came to my door, she looked very different than I was used to. She’d fixed up her hair, and was wearing a cute little outfit with a pink scarf, it made her seem very girlish and it was a good look for her. I was glad to see her. We’d been texting all week, and although we’d discussed being careful not to get emotional, we were enjoying ourselves. I sat her down on the couch, got us some drinks, and we chatted for a while.

Soon, our dinner was ready, and I ran out to pick it up, from a restaurant around the corner. She was excited, she had never tried the place, and she picked out a show she liked for us to watch while we ate, hoping I’d like it, too. It was a medieval fantasy, and she was embarrassed to admit she was addicted to it. “It’s the only weird show I’m into,” she said, defensively.

“It’s not weird!” I promised.

We kissed, and as she finished her meal, she climbed onto my lap. Soon, the show was over, I was hard, and she was unbuckling my pants again. As she slipped down between my legs, she asked me if I could go twice tonight. “With you?”

She laughed and took me into her mouth again. Her eyes were very green, and she stared right into mine as she worked her lips and tongue down the underside of my shaft. She clearly wanted to show off, and took me deeply, then sucked my balls and started licking lower and lower until her tongue was close to my asshole. I’d never had that before, and it made her giggle to hear it.

“Everybody in the music industry kind of just sleeps with whoever, I used to get a lot of practice at this.”

Soon, she had me so worked up that I stood up and grabbed her by her hair. She seemed startled, but didn’t resist as I began fucking her mouth. I was careful not to gag her – but not too careful – and her stilted whimpering ended only when I finally pulled out and began stroking over her face.

She was breathing heavy and wide-eyed, but obediently tilted her head back and stretched her mouth open. That made me cum in buckets, three thick ropes across her nose and forehead. When I was finished wiping the last drops onto her lips, she started to put her hands up to her face but then hesitated. I helped her up and walked her over to the bathroom. “I’ll get us some water,” I called.

“Water sounds good, that was hot. Oh Jesus, my face,” she called back, looking into the mirror and gasping.

We watched a movie, drank a bit, and eventually went to bed, where we were soon going at it again. This time she was much calmer. She moved slowly and deliberately while I thrust into her, touching her breasts and sighing heavily. When she tried to put her hands on my back, I held her down by her wrists. “You can’t scratch tonight.”

“Why, you have a date who’ll get jealous?”

I nodded, and it just made her giggle. When I finished, we cleaned up and fell asleep right away. It felt like it was only a moment before it was dawn with her stroking my morning hard-on and kissing my chest. She rolled on a condom and climbed on “reverse cowgirl”-style. I was still drowsy, but mornings take me a while, and I quietly watched her ass pumping until her greedy little pussy milked another orgasm out of me. Then it was time for her to go home and for both of us to get our days started.

A few days before our next appointment, Kelly told me she had met someone, D. She wasn’t sure if it was serious, but she wanted me to know. She was fucking him, she said, and being safe. “If you start seeing somebody, how am I going to take you on a vacation somewhere?” I teased.

“Hah. If you take me on vacation, I’ll do whatever you want.”

“You sure about that? I can imagine a lot for ‘whatever’, your little friend would be pissed.”

“LOL. I’d never tell on you.”

I wasn’t hurt, but it was a bummer. I knew our fun would come to an end eventually but I didn’t know she was shopping for a relationship so soon. I joked with her about how I’d have to take her against her will. She thought it was a fun idea, and when she came by to clean next, I didn’t hesitate. I let her finish her work before I entered the kitchen, and when her eyes met mine, I pushed her down over the island, face-first. She laughed and pretended to struggle, then pushed her hips back to meet me.

Unbuckling my pants, I reached down and unzipped her shorts, pushing them and her panties down to the floor. Blue and lacy, she’d planned on getting a good fuck today. I put a heavy hand on the back of her head and held her down on the island by her hair, using my forearm and elbow on her back to pin her down, rubbing her pussy with my free hand. “You were wearing those for me?”

She laughed playfully. “Maybe I wore them for D.”

“He’s going to be disappointed if they’re smeared with my cum.” I held her down harder in mock anger and grabbed the condom on the island. When she tried to struggle again, and I spanked her once, hard, making her yelp. “You should stop fighting this, Kelly. You can only make me so hard.”

“You’re a pig!” she laughed.

I spanked her again, harder. The noise she made was more of a cry. “You love it. When was he last inside you?”

“Last night. I came here from his house.”

“Does he know what you’re doing?”

“No. He knows I hooked up with some guy I clean for at some point, but I told him it was just a one-time thing that happened.”

I lined the head of my cock up with her tight little pussy. “How does he like that you’re cleaning my apartment right now?”

“He claims he doesn’t care, but he keeps texting my phone.”

Her phone was on the counter behind me, and I looked over. She was right. Her phone was charging, lit up and vibrating. I could feel how hot and wet she was from resisting, and I pushed inside her, very forcefully, balls-deep in one slow motion. She yelped and I could see her grit her teeth, then strain against me. With my left hand still clutching her hair and resting down her spine, I reached beneath her body with my right and teased her nipples, letting her get used to my size before I wrapped my hands around her neck and started pounding. I’d ease up sometimes, to tease her clit with one hand, and she said very little until she couldn’t speak at all. After a few minutes, I emptied my balls then rested with my cock still inside her, my weight bearing down on her to keep her in place, kissing the back of her neck before finally pulling out slowly and letting her up. As she stood, there was an obvious red spot on her forehead where she’d been pinned against the island countertop, about the size of the palm of a hand. I warned her not to let her new boyfriend see it, but she laughed it off. She was going home to her place, not his. We hugged and kissed goodbye at the door, and I gave her a slap on the ass with her cash on the way out.

After that, we stayed in touch, but she was distracted. I could tell she was hot-and-cold to D. She would fall out of touch for a few days, then apologize and vent about him. By the time she came to my apartment again, she thought things had gotten serious. Some of the things she said raised my suspicions that D was a total piece of shit, but I minded my own business. Kelly appreciated it, and although we kept texting, we stayed away from sex.

A couple of months later, while washing my dishes, Kelly blurted out “D and I had a threesome.”

I was working at my desk, and I wasn’t sure what I was supposed to do with that. “With your friend you told me about?”

“No, it was a friend of his I’d gotten to know, a girl.”

Being myself, I wanted details and she told me the story. From the sound of it, D had been pushing for it and it didn’t go well. She meant to complain, but the vivid image of her and a blond sharing a cock stuck with me, and when she stepped into my bedroom to change my sheets, I couldn’t help myself. When I came to the door, she seemed upset, like it was on both our minds. She could feel that I was hard. “I can’t do that anymore.”

“Are you two serious or are you just fucking around?”

“Yes… I don’t know.”

I felt bad. She didn’t mean to start anything and I realized I was taking advantage of her confiding in me. “We can’t have conversations like that when you’re here apartment if we can’t act on them. You know how much you get to me.”

“I know, I realized it as soon as I said it. I’m sorry.” She sighed and started fumbling with my belt buckle. “Fuck it.”

I was surprised. “You don’t have to do that.”

She didn’t say anything, she just unzipped my jeans, then took her shorts and top off. She laid down on the bed she had just made, on her back, and tilted her head off the edge of the bed toward me. I knew what she had in mind, and as I reached out to run my hands down her body, she opened her mouth wide for me. I slipped a hand inside her panties to finger her, and she moaned and put her hands on my hips. She was wet and warm, she’d been wanting it, too, and with her face buried between my legs, I began to pump away at her mouth slowly. Soon she was pulling me in deeper with her hands. I could feel my balls striking her face and hear her choking a little, until she pushed back and unwrapped her lips to speak. “Just do it. Use my mouth. Fucking punish me.” She was almost spitting the words, and that was all I needed to hear to put any hesitation aside.

When I began thrusting, she gagged hard, bucking and twisting her head around the fat cock, climaxing as I busily worked fingers inside her. Soon I could feel she was nearly swallowing all of me, and I could feel my own orgasm building, in part at taking a little satisfaction in the thought of D’s helplessness about his little girlfriend. I think that’s what she wanted, too. I stood up and cradled her head in my hands, pushing a little deeper to encourage her to take me all the way into her throat. I could feel that she was trying hard, and the noises changed from moans and slurps to gagging, then bouts of silence as I pushed into her throat too deeply for her to exhale. I thought of pulling back, I couldn’t see her eyes to tell if she was running out of air, but she was grabbing my ass tightly, moving her tongue, and wouldn’t let me back out. Realizing that she wanted me to choke her made me cum, hard. I could see her whole body tensed up across my bed as my cock twitched in her throat, but she didn’t let go of my ass until I was done. That was when she she moved her hands and pushed me away, messily freeing my cock from her throat and looking away, gasping for air. Spit dripped onto her face, she had tears in her eyes, and was so visibly spaced out that I couldn’t help but take the moment to give her a slap across the face. Not too hard, but hard enough for her to look a little fearful when she saw my hand draw back, then for the strike to bring her back to the real world. “You wanted to be punished. You feel the way you wanted to feel?”

She nodded, then got up, put her clothes on, and quietly took her check from the island. We hugged, I ran my fingers through her hair, we made out a little, and she left. Before long, she moved in with D and I did not hear from her again.

Source: reddit.com/r/gonewildstories/comments/a7ezn7/stretching_out_my_housekeeperf