I Was Asked to Stay

“You’re back,” I said from the kitchen, setting down a pan to dry. “Already?”

Dan tossed his keys on the counter. “Regrettably,” he said, somewhat defeated.

“Well,” I said, scrubbing at a plate. “How was the date?”

Dan opened the fridge and grabbed a beer.

“Oh,” I said, “that kind of date. Sorry.”

Dan had been one of my instructors at university. Despite being more than twice my age, Dan and I had a lot in common. I had babysat for him once, mostly just to earn his favour during school, and ever since he would reach out any time his regular sitter wasn’t available.

“We just didn’t click,” Dan said. “No harm there.” He lifted a beer in my direction.

“After I finish these dishes, thanks,” I said and smiled.

He popped the cap on both bottles but set mine to the side. “How were things here with the girls?”

“Simple, as always. You just missed them,” I said, looking at the clock, “they fell asleep about twenty minutes ago. So, tell me about the date.”

“Tara was nice,” Dan said.

“And a total babe, from the picture you showed me earlier,” I added. Even though it had been a compliment, it seemed to sting at him.

“Absolutely,” Dan agreed. “It’s alright. I’m not looking for anything serious right now, anyways.”

“No?” I asked, setting down the last dish and drying my hands. I took a drink of the beer.

Dan started to say something, then pointed at my feet. “I like the choice of colours.”

“Oh,” I laughed, “the girls wanted to paint nails, and I let the choose the colours. A bit of a—distracting palate, I’ll admit.”

Dan sat down on one end of the couch, and I took a seat at the other. “I like them. Thanks again, for being willing to babysit on such short notice.”

“It really isn’t a problem. I didn’t have plans tonight, anyways. You know, I told you I would be here until midnight,” I said, “if you want to go relax. I’ll keep an ear open for the girls.”

“I was hoping Tara would help me relax,” Dan said beneath his breath. “Sorry, bad joke.”

“It will take a lot more than that to offend me,” I smiled.

“It has just been—awhile, since I’ve—” Dan started, looking for the right words.

“Fucked?”

“Stephanie!” Dan grinned.

“Sorry! I have a terrible vocabulary sometimes. You know this.”

“That’s true,” Dan agreed. “I was going to say, since I’ve been intimate. Not that I should be telling you that. It can get, frustrating, you know? But no, you can take off. I’ll probably just get to bed early.”

“Now I just feel bad,” I said. “You know—you did pay me to be here until midnight,” I whispered sexily, but joking.

“Aside the fact that I am old enough to be your dad,” Dan started.

“I’ll call you daddy,” I jested.

“Don’t take this the wrong way, you’re cute, but not exactly my type.”

“Blonde?” I asked with a knowing smile.

“Exactly,” he lied. I knew he wasn’t into transgirls, that was okay. Everyone has their preference. But something about it bugged me, and I didn’t know why. My pride, possibly?

“Alright. Well, I’ll get out of your hair then,” I said. “I’ll just grab my bag, I put it in your room, I hope that’s okay. Didn’t want the girls rummaging through it.”

“Not a problem,” Dan said. “Thanks again for watching them.”

“I don’t mind at all!” I said, tossing my empty bottle. “Sorry again about your date. I know the feeling—not that great. Let me know if I can do anything to help.”

I tiptoed up the stairs and into the bedroom where I had stashed my bag against the far window. I had slung it over my shoulder and was checking my texts for a minute when Dan walked into the room behind me.

“Oh,” I jumped, putting a hand over my mouth, “sorry, didn’t see you there.”

“I—um, I wanted to apologize for saying you weren’t my type. I fear it came out rudely,” Dan said.

“Don’t even think about it, Dan. I get it. Honestly, didn’t bother me,” I said. Much, I thought.

“And I was thinking about what you were saying,” Dan continued.

“Yeah?” I said, my attention pulled toward my phone.

“There is something you can help me with.” Dan closed the door behind him.

I froze in the middle of the room where I stood. Dan walked over to me and set my bag down. I stood there with a look of confusion, waiting for him to make a joke. He was so tall when he stepped in front of me.

Dan gently held my jaw with his hands, lifting my chin and kissing me. Softly, but sweet. His scruff brushed against my lips. I liked the speckles of grey fading into the corners. Did—did Dan just kiss me?

He started to unbutton his shirt, but I pushed his hands away, doing it myself. I ran my hands along his bare chest, the curls of his hair catching beneath my fingers. Dan tossed the shirt on the bed, then he pushed on my shoulders until I was on my knees.

I held onto the sides of his belt, teasing out the moments as I unlatched it. When I undid his zipper, he pushed my hair away from my shoulders so that it hung along my back. My heartbeat picked up. He pulled out his cock before I could grab it, giving it a few strokes in front of my face.

My fingers were cold when I grabbed hold of his warm shaft. Dan was thicker than I expected, and oddly wrinklier, not that it really mattered to me. A part of me was turned on by how much older he was than me—and a little curious.

I stroked him with both hands ever so gently. He watched me, leaning down to tuck the hair behind my ear. I held his cock against my outstretched tongue, continuing to stroke him. A bit of precum dripped, so I locked my lips around the tip.

Dan grabbed my hands lightly and put them to my side. I still held the tip of his cock in my mouth, looking up at him. He put his hands on my jaw again, then pushed his cock a little further into my mouth. I let him decide how he wanted it.

It seemed like he was testing it at first. He pushed against my tongue, then my cheeks, then slowly pushing further down my throat. I kept my hands at my sides. He pulled on the back of my head until his cock couldn’t go any further down my throat. I gagged for just a second but fought against it.

“That’s a good girl,” he whispered.

I kept deepthroating him, until spittle dribbled from my chin. He bent over and pulled off my shirt, then lifted me to my feet.

“Lay on the bed,” he said.

I walked backwards, unstrapping my bra but not letting it fall off. I bumped into the bed, then jumped up onto it. Dan set me on my back, my legs still hanging off the bed, then took off my bra. He kissed along my neck, then started to suck on my nipples. When they got hard, he bit down on them tenderly.

I was almost surprised when he unbuttoned my jeans and started to slide them off. I fixed my panties as he struggled when my jeans got to the ankles. When they were off, I pressed my bare feet against his chest. I liked the way his coarse hair brushed against my soft soles.

He grabbed my ankle, then licked along the edge of my smooth heel. I bit my lip and suppressed a moan. He kept licking upward, between my toes until he was sucking on them. Then he let go of my ankles and looked at my panties.

I hid my transcock from him.

He grabbed something from the nightstand, then spun me onto my stomach. I pulled my transcock to the front as he slid down my panties and held my cheeks open. I had to stand on my tiptoes to reach the ground.

I heard a crinkle of plastic and looked back to see Dan putting on a condom. He’s going to fuck me, I thought excitedly.

He pushed his cock into my tight asshole, grabbing my waist. I rested on my elbows, savouring the pain of being split in two by his dick. He reached for my boobs, squeezing as he thrust inside of my asshole. I could feel the slap of his balls against me.

“Get on the bed,” Dan whispered, noticing me struggle to stand off the edge. I got on all fours as he mounted behind me. I held my transcock against my stomach so he wouldn’t see as he put his cock back into my ass.

He put a hand on the back of my neck and lightly pushed me down into the bed. I grabbed a pillow and moaned as he slid back into me. I tilted my head and watched over my shoulder as Dan, breathing heavy, pounded me from behind.

Dan slapped my ass. It stung and I yelped with pain and pleasure. My asshole thwapped as he pulled out entirely, leaning on the bed clearly tired.

“Here, lay back,” I whispered, then mounted him reverse cowgirl. I held tight to my transcock as I started to ride.

I leaned forward, putting my feet on his chest as I took him. Dan rubbed at my soles, grabbing my ankle and bringing my foot closer. When he started sucking on my toes I moaned loudly, then covered my mouth with my hand.

I held his sack with one hand and my transcock with the other. Dan put his hands around my waist and shoved me down with each thrust. I gasped as my breath caught in my chest.

“Oh fuck,” I whispered, “fuck.” His cock hit just right, and I felt my transcock starting to throb. I cummed in my hand, hiding it.

Dan groaned and held me down. He stretched out and I could feel his cock throbbing inside of me. His arms went limp and fell to the sides of the bed. His chest heaved beneath me, then he started tenderly stroking along the edge of my hips.

I lifted off his cock and spun around onto my stomach, laying between his legs. The tip of the condom was bulging with thick white cum. I gave his cock a few more strokes, then worked off the condom. Dan just sat back and watched as I poured the cum into my hand. I was hoping he wouldn’t notice my cum already in there.

Warm cum collected in the palm of my hand. I let it drip over Dan’s cock but keeping it on my hand. He watched as I licked up the cum, playing with it in my mouth before swallowing.

I rested my head next to his cock and looked up at him. “So,” I whispered, “you still think I’m not your type?”

“I haven’t fucked like that in a long time,” Dan whispered.

“Dan! Language!” I whispered harshly though joking.

“I can’t believe we just did that,” he said.

“You can’t? Should we do it again, so you know for sure,” I jested. I looked at the clock. “I mean, I am technically here for another hour.” I started to stroke his cock against my cheek.

“I don’t know if I can,” he laughed.

I kept my eyes locked on his, then put his cock in my mouth. I pushed it down my throat, still looking at him. He put a hand on the back of my head and pushed me down a little further. When I pulled back his cock was firm again.

“Think you’re ready now?” I asked, a string of spittle connecting my lower lip to the tip of his cock. Then kept sucking before he could answer.