by Jane Futa
Chapter 5
I had more confidence at my next gig. Her name was Wendy and she was friendlier than both Monica and Chester combined. It was late at night so she whispered her instructions to me before she left. Despite her friendliness, I felt her checking me out the same way Chester had the day before.
In fact, when she came back, she continued to check me out. She didn’t pay me right away, either. Instead, we sat in the living room making small talk.
I was wearing jean shorts and a loose shirt this time, so I was confused about the way Wendy was looking at me. She held a mug of tea close to her lips as her eyes traveled up and down my legs. I wanted to be polite, but I also wanted to get my money and get home before my parents realized how late it was. I hadn’t told them I started babysitting and I didn’t need them finding out. There’s no way they’d believe the restaurant had me working this late.
Wendy had long, dark hair that was pulled back into a tight bun. Her green eyes filled with lust the longer we spoke. A few times, my voice slipped into a lower register on accident and I caught her smiling at me.
“Tell me, Nicole,” she said. “How long have you been a woman?”
The question terrified me. “What…what do you mean?” I said, twirling the curls of my wig like I’d seen my sister do when she was nervous.
“Come on now. You don’t actually think you’re fooling anyone, do you? You’re trans, right?” She sat down next to me and placed her hand on my bare thigh.
“I don’t…I don’t’ know what you’re-“ but before I could finish, she was cupping my groin. There was no way she didn’t feel my hard penis underneath my jean shorts. “Shit,” I moaned.
“That’s what I thought,” she said, with her lips to my ear. “You know. I’m an open minded person, but I hate being lied to. You’re one of those sneaky little sissy femboys aren’t you?”
“No. No, I’m not. I’m trans, you’re right.” She smacked my cheek lightly.
“Don’t fucking lie to me. You know what sneaky little femboys get?” I shook my head. “A nice, hard cock shoved right up their tight little ass.”
“What?”
She wrapped her hand around my throat gently and whispered, “You heard me. If you want to get paid, you’re going to have to follow me to the bedroom.”
She stood up and walked down the hallway. I felt empty without her hands touching me, even if it was the most humiliating moment of my life. I looked at the door and considered leaving, but curiosity got the best of me. If it had just been about the money I might’ve fled. But I had to know what Wendy had in store for a little sissy slut like me.
Chapter 6
I entered the bedroom and she pointed to the edge of the bed. I sat down and waited for her punishment. She walked to her dresser and pulled the top drawer open. I watched her dig around piles of lingerie until she pulled out a long, thick, black dildo.
“Fuck!” I cried with wide eyes. No human cock was ever that big. I was terrified of what she was going to do with it.
“This is for little sissies who try and fool their babysitting clients.”
“There’s no way I can take that,” I protested.
“You’d be surprised what the human body is capable of,” she said. I swallowed hard as she walked closer to me. Her black skirt stretched across her thighs as she moved and her pink blouse tightened as she bent over me. The black cock hung above my head, dangling like a carrot I was supposed to chase. “Lean your head back and close your eyes,” she commanded.
I arched my neck and let my lids fall. She placed her thumb on my lower lip and slid it in slowly. I sucked on it like my life depended on it. The smell of her lilac perfume wafted through my nose, and her skin tasted like candy.
She tugged my chin down until my mouth fell completely open. Then I felt the bulbous head of the black dick rest along my bottom lip. She pushed it in slowly and I had to work to open wide enough for its thick girth.
“Mmmm,” she moaned. “That’s a good little femboy.”
I wrapped my lips around the entire thickness of the cock. She tested my limits by pushing it further until it was touching the back of my throat. Oh fuck. This is so hot. I’d had sex before, but it was always very vanilla with semi-experienced college chicks.
This was a career woman, a mother, who was giving me the most taboo experience of my entire life. She pushed the cock deeper in until I started to gag. Then she pulled it out slowly. Each time she slid it in and out of me, she moaned as if it was penetrating her. She reached for my hand and placed it on one of her large breasts. I massaged it, still in shock of what was happening to me.
She pulled the cock out of my mouth and then grabbed my neck again. “Roll your sweet, virgin ass over,” she said. I laid down on the bed and rolled onto my stomach. She climbed above me and reached underneath to unfasten my shorts. My cheek pressed into the bedspread as I let her have her way with me.
She tugged my shorts and black panties down just below my ass. My sister had finally given me a few more pairs of lingerie so I wouldn’t have to wash the same ones every day. It was especially good since I couldn’t stop coming in her panties.
Wendy spit on my ass and rubbed her spit between my cheeks. She slid a finger deep inside me and I remembered the day with the hairbrush. I closed my eyes and bit my lip. It felt so good to be penetrated as a woman.
I felt a second finger slide into me and then a third. She thrust them in and out while moaning. She wiggled them inside me, trying to stretch my hole wider. My cock hardened with each thrust of her fingers. Then I felt the head of the large, black cock resting at my entrance. I held my breath as I waited for her to push in.
My ass split and stretched around the thick girth of Wendy’s cock. I groaned as she moved it deeper inside me. “Fuck!” I cried.
She laughed and said, “This is what sneaky femboy sluts get!” Then she stopped holding back. It was as if her own dirty talk fueled her. She started thrusting harder and faster into me until my body was moving up and down on the bed. I gripped the sheets in my fingers and nearly bit my lip so hard it bled.
“Fuck! Shit!” I cried as she pounded my ass. She moaned with each thrust and then grabbed my hand. She brought my hand between her legs and up her skirt until my fingers were brushing along her soaking wet panties. I swirled my fingers over her panties while she thrust in and out of me.
Moments later she screamed, “I’m coming!” Hearing her come while getting my ass pounded sent me over the edge. I felt my own come spill from my cock all over my sister’s outfit and Wendy’s bed. We both panted as we came down from our high.
She lay next to me in bed and smiled. “I’d love to have you babysit again,” she said. “But for now, I need to get some sleep.”
I nodded and smiled back. Then I got dressed and Wendy pulled out a wad of cash from her purse. It was way more money than I was owed.
“Oh shit,” I said when I realized she’d handed me hundreds of dollars.
“There’s more where that came from,” she said with a wink. My heart beat faster at the thought of being a sissy slut for pay. My life just seemed to get more and more exciting with each day.
We said our goodbyes and then I returned home to sis. I dropped the wad of cash in front of her and watched anxiously as her face lit up with surprise.
“Where the hell did this come from?” she asked as she flipped through the bills.
“She really liked me, I guess,” I teased.
“No way. No mom likes their babysitter this much. Did you sleep with her or something?”
I tried to keep my secret but Brianna could read it on my face. “You fucking did! Did she know you were a boy?”
“Apparently. She liked it, I guess,” I told her.
“Get out! Looks like we may have a slight change to our business plan…” I was giddy at her comment. Then my body seized up when she told me I’d be going back to Chester’s house.
“Tomorrow night. Is that cool?” I no
dded my throat felt dry. I went up to my room, but I was unable to sleep. Why did he make me feel this way?
Chapter 7
I couldn’t believe my luck when I arrived at Monica’s. Chester was the only one there. Brianna had failed to mention it to me. “I’ll be back in an hour,” he said. “I just have a business meeting and Monica is out of town. Should be a pretty easy hour.”
“No problem,” I said, twirling the white, flowing skirt Brianna let me borrow. His eyes scanned me more obviously this time, probably since Monica wasn’t around. I felt my cock grow hard and I turned suddenly so that he wouldn’t see it.
“Ok, see you soon.”
The hour flew by with ease. His kid was napping and I just watched TV the whole time. My heart stopped when the door opened. After what had happened with Wendy, my perspective on babysitting had been shifted. It was just me and Chester alone now and he had nowhere to be.
I did the bravest thing I’ve ever done. I ran up to him and greeted him by touching his arm flirtatiously. He looked at my hand and then his sparkling eyes traveled back to my face. He looked like he was going to kiss me but then he walked away quickly.
“It must get lonely here without Monica,” I said as he dug through his wallet. He exhaled as if dealing with a pit of sexual frustration. He turned around and leaned his hands on the kitchen counter.
“You know. It does. But Monica hasn’t had sex with me in like a year, so it really doesn’t matter.”
My jaw dropped. “Oh my.”
“I’m sorry,” he said, brushing a hand through his thick, dark hair. “I shouldn’t have told you that.”
“It’s ok,” I said, walking closer to him. I looked his body up and down and started to salivate. As far as I knew, he wasn’t aware that I was a boy. Am I really about to try and trap him? I couldn’t help myself, though. I couldn’t stop thinking about his muscular body and his sparkling expression.
I stepped closer until our faces were inches apart. He looked at my lips longingly. I could tell he wanted to kiss me but was holding back. So I made the first move. I leaned in until our lips were touching and he didn’t pull back.
My body felt hot and my skin tingled. Is this what it feels like to be a woman kissed by a man? It was completely different to kissing a college girl as a college boy. I wanted to be Chester’s sexy slut. I wanted to be his mistress.
He plunged his tongue down my throat and placed his hands on my cheeks. Our tongues danced and swirled. He smelled woodsy and dangerous. I wanted all of him. I wanted him to have all of me.
I moved my hands to his belt and started to tug it loose. He didn’t fight back. He didn’t protest. Instead, he kissed me harder, even allowing his hands to travel to my not-so-real breasts. He didn’t seem to notice or, at least, he didn’t care. I didn’t care either. I hoped he wouldn’t be disappointed if he did find out, but I had to try. I had to experience him. I wanted to be his slutty little femboy.
I dropped to my knees and he watched me eagerly. I pulled his slacks down with his briefs. His cock was just as long and thick as the dildo from the previous night. I started to realize maybe I was just smaller than most. My eyes widened but I licked my lips. Then I wrapped my fingers around his thick shaft.
He leaned his head back and groaned. I stared up at him, desperate to make him happy. I wanted to make him come inside me somehow. I wrapped my lips around the head of his cock. Then I flicked my tongue along the underside. He lowered his head back down to watch me. I could tell that he thought I was beautiful by the way he looked at me. My body felt warm to know that a man thought I was sexy enough for him.
My cock hardened as I slid my mouth further down. I felt him expanding inside my mouth. I took all of him in until I was gagging. He brushed his thumb along my cheek lovingly. He was amazingly sexy and yet still tender. I wanted to please him more than anyone.
I bobbed my head back and forth while swirling my tongue along his shaft. He placed a hand on the back of my head and groaned. I loved feeling him touch me like a little slut. I wanted to feel him inside of me, but I didn’t want him to know my little secret.
He wanted to be inside of me too. “Stand up,” he said before he could come all down my throat. I stood up and he kissed me. He fondled my breasts again and then spun me around so that my ass was pressed against his cock.
He lowered his hips until his cock slid up underneath my skirt. It rested against my ass cheeks which had a black thong between them. I felt the fresh, clean skin of his cock press against my cheeks and I cooed. I was desperate to feel him inside me.
He reached a hand under my skirt and pulled the strap of my thong out from my cheeks. Then he leaned me over the kitchen counter and lifted my skirt up above my hips. I bit my knuckle, anticipating that he would find out my secret. I was afraid, but the fear made everything that much more pleasurable.
I didn’t care anymore if he found out. If he did, it would be just as exciting. Wendy had changed me. She made me love the humiliation. She made me love the submission. All I wanted now was to please whoever I was with as a little femboy.
He rubbed his shaft between my cheeks. “Have you ever been spanked?” he asked while leaning over me. I shook my head. “Allow me to give you a little taste.” He lightly spanked me and I cooed in delight. “You like that?” I nodded. He spanked me harder and I moaned. “That’s my good little slut.”
I blushed when he called me a slut. It felt so good to have him like this, especially knowing he had a wife who no longer pleased him. He deserved to be pleased, and I felt lucky to be the one to give him pleasure. He spanked me harder and then slid his cock between my legs. When it grazed my balls my eyes shot wide open.
Fuck. There’s no way he still thinks I’m a girl now.
“What the?” He pulled his cock out and inspected between my legs. “Well what do we have here?” he asked as he massaged my balls. I wanted to pull away out of embarrassment, but I couldn’t. Feeling his hand on my balls felt so good. “What are you some sort of trap?”
I bit my lip and nodded. As humiliated as I was, I was turned on more. I didn’t care if he threw me out. I didn’t care if he told his wife or if I lost my job. I wouldn’t have given up this experience for anything.
“I’ll make a deal with you,” he said. I listened closely. “I won’t tell my wife about your cock if you don’t tell her that I fucked you.”
“But you didn’t…” Before I could finish, he was sliding his cock deep into my ass. “Oh,” I moaned. He grabbed my hips and slammed his cock into me over and over. My body slid back and forth across the kitchen counter.
He pulled my hands behind my back and held my wrists together. Then he placed one hand on my shoulder to keep me in place while he slammed into me. My hard cock bounced against the side of the kitchen cabinet. I knew I was going to come at any second.
Just then, Chester screamed that he was going to come. “I’m going to fill your little sissy ass with my hot load,” he warned. That’s when I exploded. My come dripped down the side of his cabinet as he unleashed his load inside me. My ass felt warm suddenly and a drizzle of hot liquid spilled out down my thigh.
My head was spinning and I was grateful to be pressed up against something so I didn’t faint. He collapsed over me, panting. He waited a few minutes before pulling out. He held me in his arms while he waited. I was surprised by his sudden tenderness.
“I hope this doesn’t push you away,” he said, finally. “I hope I can see you again.” I started to realize just how lonely he was. Or maybe he just really liked me.
“I don’t want to stop seeing you,” I told him. He smiled and pulled his cock out. We both dressed ourselves and laughed off the situation.
“You’re really beautiful, you know,” he said. My heart melted in my chest. I stayed with him as long as I could and he gave me another large sum of cash similar to Wendy’s. “Please don’t tell my wife,” he whispered.
“Your secret is safe with me.” I smiled and we said
goodbye.
Chapter 8
From then on I was known as a special kind of babysitter. I was secretly called the Femboy Babysitter. I felt like I had some kind of superhero nickname. I felt powerful and sexy. I still sat for Chester often. He fucked me whenever we got the chance. I think he started to fall in love with me the moment he found out I was a sissy. A part of me fell in love with him when he told me I was beautiful despite that.
I saw Wendy frequently. I told her my stories about Chester and any other femboy experiences I had. She almost liked listening to my stories as much as she liked dominating me with her big, black dildo. I became very close with her.
By the end of the summer, Brianna and I had earned way more money than two babysitters should have. She never had to hire any other girls because I raked in so much cash. I loved my new lifestyle so much that I finally told Brianna she could post photos of me to social media. Of course, I had to come out to my parents first.
That was a strange conversation, but both Wendy and Chester had given me the confidence to be a full time sissy. Brianna stood up for me each time my parents tried to argue about it. I became eternally grateful for Brianna and we’d never been closer. I loved having a little sister that cared about me that much.
She and I planned a day to have a photo shoot in a bunch of new outfits. She took me shopping for my own clothes and then we drove from place to place to take pictures. She helped me pick out the most flattering images and then I submitted them to all of my social sites.
She held my hand while I waited to see the responses. Some were critical, of course, but I received an overwhelming display of support, especially from my gamer friends. I couldn’t believe how many of my friends still accepted me. They teased me a little bit, but I didn’t really mind. I could tell it was out of love and I still enjoyed the humiliation.
Soon, I realized how pivotal social media would be in helping me find more clients. Of course, I never did tell my parents about the babysitting gig. I figured one piece of bad news at a time was best.