by Jane Futa
I ran up to my bedroom and opened my suitcase. I dug through the clothes for the flesh light I had bought myself in college. It was the first time I had an address of my own to ship it too, so it was one of the first things I bought after moving. I squirted a small amount of lube inside and then pulled out my cock.
“Oh, Wendy,” I moaned as I slid my cock inside the toy. I imagined her dress up around her hips, bent over the trunk of her small car.
I imagined her saying, “We shouldn’t be doing this. We’re outside where everyone can see and you’re my son’s best friend. This is totally wrong.”
“I know, and I don’t care. I have to have you,” I said as I slid my cock in and out of the toy. I pictured my cock sliding in and out of Wendy’s beautifully trimmed cunt. As I fucked her, I pictured her breasts pressed against the car and her body shifting back and forth over them.
“Oh yes!” she cried. I slid the toy over my cock faster and harder. Minutes later I felt it fill up with my warm, sticky come. I wondered if it would feel the same to come inside of her perfect little pussy.
Chapter 2
My parents got home late that night and decided to take me out to dinner. They were happy that I had passed my first year in college and were looking forward to me getting my degree as soon as possible. They were also happy I was home, but I got the feeling that their romance bloomed once I left the house. I did not want to imagine to what extent.
It was interesting that the same year my parents were rekindling their relationship, Mrs. Matthews had been divorced. I couldn’t help but wonder if she was dating anyone or if she even wanted to. I could only picture her with alpha men like her ex-husband, but I wondered if she would ever try to go in a different direction. I knew if she ever were to ask me out I’d say yes in a heartbeat. Only if I wasn’t friends with Bryce anymore.
I never would want to sacrifice my friendship with Bryce anyway. We had grown up together since kindergarten and were really close. I knew the summer was going to get boring pretty fast if he worked all day. I tried to think of what I could do to pass the time.
“So what are you plans for the summer?” Dad asked once we were sitting down at the restaurant. I looked around lazily as if my answer would appear in one of the nearby booths.
“I’m not sure yet. Most of my friends are doing their own things, it seems.”
“You could get a job like your friend Bryce,” said Dad. Mom kicked him under the table and frowned at him.
“He just got back. Let’s let our baby enjoy himself.” She smiled and winked at me before taking a bite of her cucumber salad. I slouched. I hated when she called me baby. I felt emasculated enough without having my mom think of me as an infant all the time.
“I’m just saying. It’ll look good to future employers if you were to get some kind of summer job. It would also keep you out of trouble.”
“What kind of trouble do you think he’s planning to get in?” asked Mom with a raised eyebrow. She was always jumping at my defense which I guessed was a result of me being an only child.
“He’s a nineteen year old boy. Trust me, there’s plenty of trouble out there for him.”
To shut them up, I came up with the first thing that popped into my head. “I’ll see if there’s a position where Bryce is working. Next time that I talk to him I’ll ask if he can put in a good word for me.”
Dad shut up immediately and nodded toward me. He respected my answer and my mom smiled. I knew she’d enjoy the thought of me working close to Bryce. It would seem safer to her.
We finished eating and went back home. My parents still had work in the morning so we all went to bed early, but I had no plans to sleep just yet. I rushed up to my bedroom window and peered through the blinds. Mrs. Matthews hadn’t changed a thing. She was in her bedroom across the street with the curtains still open.
I quickly dashed my dresser and pulled out a pair of binoculars I’d always kept for just such occasions. I noticed there was a car in the driveway that wasn’t hers and wasn’t Bryce’s.
Maybe I’ll get a chance to see what kind of guy she’s into, I thought. I rushed back to the window and held the binoculars up to my face. I peered through the glass cylinders toward her window and nearly pissed my pants.
Mrs. Matthews was fully nude and standing next to another girl. Holy shit. Is she a lesbian? I watched closely. The other woman was in lingerie and Mrs. Matthews was kissing her. Her tongue slid down the other woman’s throat and she reached between the other woman’s legs.
“This is fucking hot,” I thought. I was slightly disappointed that Mrs. Matthews may no longer be interested in men, but I’d never seen two women making out before. It was every guy’s fantasy. I watched them caress each other and moan. My dick grew harder the longer I peered at them.
Mrs. Matthews sat on the edge of the bed and reached for the other woman’s panties. She tugged them down and I couldn’t believe what I saw.
“She has a cock!” I cried out. I quickly covered my mouth for fear that my parents had heard me. I listened closely for a reaction from them, but the house was silent. I peeked back at the room to see Mrs. Matthews sucking off the other girl’s cock.
I couldn’t really figure out what I was watching. Was it a girl with a penis? Was it a trans woman? Was Mrs. Matthews really into this? Despite knowing there was a cock in the equation, I was getting harder by the second. A sudden wave of guilt washed over me as I reached into my pants and gripped my cock.
I can’t jerk off to this, can I? This is too strange and weird. I didn’t feel good at all about it turning me on, but I couldn’t deny how hard my dick was. I felt it growing more and more every second and my pants started to feel tight. I stroked my cock slowly as I watched Mrs. Matthews suck off this strange woman.
She slid her mouth up and down on the woman’s cock for only a few minutes. Then she stood up and pushed the girl onto her stomach on the bed. She walked to her nightstand and pulled out a long dildo. Where is she going to put that thing?
I quickly realized. She moved behind the other woman and spread her cheeks. I saw her rub some lube between her ass cheeks and lick her lips. Am I really watching this? Is she really going to fuck that girl in the ass?
It felt so wrong to watch, but I couldn’t look away. My cock wanted to see more. My curiosity was peaked. I had to see the strange scene unfold.
She slid the cock into the girl’s ass and I watched her writhe on the bed. The cock was huge and the girl was so small. I didn’t know how she was taking it all in. Mrs. Matthews pumped it in and out, moaning as she did. She was getting off to fucking her.
I tried to reconcile this image of her with the sweet Mrs. Matthews that I had always known. She seemed so much more dominating and controlling. It was as if she was the new alpha, and this girl was at her mercy.
I tugged my cock faster while I watched. I couldn’t believe I was getting off to the scene that unfolded before me. For a few minutes, I didn’t even care that it was turning me on. I tugged harder and harder until a disturbing image came to my mind.
I imagined I was the girl on the bed receiving the cock in my ass. The image flashed quickly and then I turned it away. But it was so hot that I willed it back to my mind. It’s just a harmless fantasy, I told myself.
I watched Mrs. Matthews ass fuck this new girl and pretended she was ass fucking me. I tugged harder on my cock as I watched. I felt it throb in my hand and my body tensed. I spilled come all over my bedroom carpet.
I closed my eyes while I caught my breath, trying not to process what had just happened. I didn’t want to even think I could be turned on by such a strange fantasy. I curiously looked back to the room and saw the girl dressing herself. If she had come, I’d missed it. It led me to thinking about Mrs. Matthews and if she had come.
I watched the girl quickly leave, as if they weren’t together at all. Then Wendy’s gaze looked straight toward my window. I panicked and hurried toward the back wall. She didn’t see me, did she?<
br />
I had decided that was enough crazy fun for the night and laid my head down to sleep. I tossed and turned. I kicked my blankets off and pulled them back on. No matter what I did, I couldn’t stop thinking about Mrs. Matthews shoving that huge dildo up some girl’s ass. I couldn’t stop wondering what it felt like and how curious I was to find out.
“Don’t be a weirdo,” I told myself as I lay in bed. But the only time I finally fell asleep was when I let my mind linger on the image of Mrs. Matthews fucking me.
Chapter 3
The next day I was alone again. My parents were at work and I was busy distracting myself from the strange night I had. I tried playing video games, hanging out social media, but no matter what I did my mind kept thinking about Mrs. Matthew’s little date.
I grew more and more curious and decided to go to a transgender porn site. I had to see if this stuff really turned me on or if it was only Mrs. Matthews. To my relief, the porn was only semi erotic to me. Sure, it was interesting that chicks had dicks, but there was something even more special about Mrs. Matthews, my dream girl, being in charge.
I had just closed my laptop when I heard a knock on the door. I looked out of a side window and saw Mrs. Matthews standing there. My heart started to race as I remembered her looking toward my window the night before. Had she seen me?
I opened the front door slowly and smiled weakly. “Uh, hi, Mrs. Matthews.”
“Oh, Neal. I thought I asked you to call me Wendy. Especially now that I’m divorced. I hate hearing the name Matthews.” The dominance from the night before showed a little through her anger. I got a chill down my spine and my cock hardened.
Not now, dick, I told it, trying to will it to go down. “What’s up, Wendy?” I asked her.
“I was wondering if you gave any thought to helping me around the house. I really could use a pool guy and a lawn guy. If you’re interested, I mean.”
I wanted to say no, but deep down I’d do anything to be closer to Wendy. I nodded slowly and she clasped her hands together. “Oh great! Well just come on over when you’re ready.”
I cleared my throat. “Uh, I can come now.” She smiled with a hint of mischief. I locked my front door and followed her over to her house, watching her ass shake in her high waisted shorts.
She showed me how to clean the pool and start the lawn mower. I decided to start with cutting the grass so that I could finish by the water. She watched me the entire time which made me feel special and slightly uncomfortable. Any other time, I would’ve loved being watched by her as I mowed the lawn, but not after the night before. I still wasn’t sure if she had seen me watching her, and I kept waiting for an awkward conversation to come up about it.
It never did, though. I eventually moved on to working on her pool and she watched me out there too while she sunbathed in her swimsuit. She was laying on her stomach, giving me the perfect view of her ass, but I could only think of a dildo going in and out of it.
“I think I’m all finished,” I told her when I had scooped up the last few leaves floating on the surface of her large pool. “Unless there’s something else you need me for?”
She leaned up from her lawn chair, lowered her sunglasses and smiled. “Nope. That’ll be all. Thank you so much. If you want to take a shower here, you’re welcome too. I’ll have the money ready for you when you hop out.”
I gulped. Shower? At Bryce’s house when Bryce isn’t home? Just me and his mom? It wasn’t that I really thought anything would happen, but the possibility of it was enough for me to agree. I headed inside, stripped myself of all my sweat covered clothes and hopped into the shower.
The shower felt nice and relaxing as it dripped over my hot skin. I scrubbed myself clean and was just about to turn the water off when I swore I heard the door crack open. I grabbed a corner of the shower curtain and looked around. Sure enough, Wendy was standing there watching me.
“Don’t mind me,” she said. “Remember that time you walked in on me in the shower?” She laughed. I felt embarrassed, but I was glad she took it so lightly. I nodded and smiled.
“Well, I thought you owed it to me to let me see you naked in the shower,” she teased. I stared at her, our eyes locked. She started fanning herself as if to suggest she was hot.
I delivered my next few words very carefully. “You can come in here if you want,” I said as if I were only joking. I even threw in a chuckle afterward. She looked at me inquisitively as if trying to discover what my words really meant.
“If you don’t mind…” she said. She was already reaching for her swimsuit straps and sliding them down her shoulder. I swallowed and tried to still the fast beating of my heart. Moments later, her breasts were revealed to me. I had become used to every shape and curve of her breasts and nipples, but she didn’t know that.
She dropped her swimsuit further to the floor and stepped out of it. Her patch of pubic hair was just as neatly trimmed as the last time I had caught her naked. She walked closer to the shower and I felt my nerves shaking. She stepped one foot in then the other, until her entire body was being soaked with the same shower faucet as my body. We were inches apart, her nipples practically touching me, but I didn’t have the balls to kiss her.
So she leaned in and kissed me instead. Her lips were soft and my head instantly felt as if it were floating on a fluffy cloud. I knew that nothing could ever make me as happy or euphoric as her kiss did. It was heavenly. It was perfect. It was dominating yet soft. It was forceful and daring, yet feminine. She had two completely different sides to her that she knew all too well.
She grabbed my hands and placed them on her hips. Then she straddled one of my legs and started to grind against the thigh. As we kissed and she rocked her hips, she reached for my small cock and started to stroke it.
I groaned through our kissing. Having her wet, naked body pressed up against me while she stroked my cock was what my dreams had been made of all these years. I couldn’t believe I was actually making out with her. Part of me wondered if I would wake up any moment. Part of me knew I was way too turned on to still be sleeping.
She started to come on my thigh and hearing her quivering moans made it harder for me to hold back. Moments later, I released my load into the shower with a low groan. She smiled as I came and laid her head against my shoulder. I held her in my arms and kissed her cheek.
I was more in love with her than ever. It had officially moved beyond a simple high school crush. We climbed out of the shower and toweled ourselves off. She kept looking at my body and my semi-soft cock with curious eyes.
“I just realized that you don’t have any clothes to wear,” she said. I hadn’t realized it until that moment, either.
“Shit,” I said. I didn’t want to put on my sweaty clothes since I had just showered and Bryce was a few sizes bigger than me. I could borrow a shirt from him, sure, but he didn’t have any pants that would fit me. “I guess with a belt, I could…”
I noticed just then that Wendy was smiling. “I have another idea…if you’re open minded,” she said. I was afraid I already knew what she had in mind…
Chapter 4
I followed her to her bedroom and saw a few outfits hanging on the back of the door. It made me wonder if she had planned this all along. But how could she have known I’d be curious enough to agree?
Maybe she was tougher than I realized. Maybe rejection didn’t really scare her the way it did me. I imagined after a divorce you’d become a little braver with relationships.
She tossed me a pair of white lace panties and a cute little bra. I thought about the girl from the other night and eagerly put the panties on. It was the most incredible feeling of my life. The delicate fabric slid gently up my legs until it was cradling my cock and balls perfectly. I fumbled with the bra for a minute before Wendy realized. She quickly came over to me, carrying another item of clothing.
“Here,” she said, handing me a pink dress. “Try this on.” She acted as if I wouldn’t protest or question her, and s
he had been right. I would’ve done anything for Wendy that she asked me to. I might even kill a man for her. She fastened my bra quickly and then returned to her position in front of me, watching.
I unzipped the pink dress and started to step inside of it. As I pulled it up over my girlish hips I heard her chuckle. “What?” I asked, feeling slightly humiliated. Was this all just some big joke?
“Well, it’s just…you coming in my shower just now. It reminds me of this time I found a wad of come covered toilet paper in the trashcan. It was about a year ago.”
I blushed. She had found it.
“Don’t worry. I cleaned it up so Bryce wouldn’t see it.” She winked at me and I continued getting dressed. I struggled with the zipper so a naked Wendy came up behind me to help. “These things are such a pain in the ass.”
I laughed and she stepped back to view me. “You could make a very sexy woman.” I turned my head to the side and caught sight of my reflection in her vanity mirror. She wasn’t wrong. My hips did the dress justice. My legs suddenly looked feminine jutting out from underneath the skirt. I couldn’t believe how womanly I looked.
“Do you mind if I feminize you a little more?” I panicked at her suggestion. More how? Like makeup? But I remembered how she fucked the girl from the night before and how the girl had a dick like mine. I nodded, unsure of why exactly I wanted that for myself. All I knew was I couldn’t deny my feelings and curiosity.
I watched Wendy dress herself in a floral skirt and a halter top. Then she went into her closet and dug around for a few minutes until she pulled out a short, black wig. “I think this would look perfect on you,” she said. I blushed as she placed it on my head. I felt the strands brush against my cheeks and fell in love with the feeling of having longer hair. It was a length I knew I could grow mine out to fairly easily. I started to toy with the idea.