It had been two weeks since that fateful night I babysat for the Holt’s. I was still trying to process what happened, and what it meant. For the first eighteen years of my life, I had never thought about having sex with a man; I thought I was 100% straight. For the first time in my life, I masturbated thinking about a man. In fact, since that night all I had masturbated to was Mr. Holt. I hadn’t heard anything more from the Holt’s, so I was beginning to turn my thoughts back to girls my own age.
Wednesday afternoon, the phone rang, and I picked up, saying hello.
“Is this Kevin?” the caller asked, and I immediately recognized Mrs. Holt’s voice.
“Umm, yes, hi, Mrs. Holt” My heart was pounding, and I was afraid she was mad at me for wearing her clothes or for having sex with her husband.
“We need you to babysit on Saturday. Come over at 3pm, it’ll be a late night, so plan on spending the night.” I picked up that she wasn’t asking but rather telling me I was going to babysit. That didn’t sound like her, but rather her husband talking. I suspect he coached her on exactly what to say. Regardless, I didn’t protest, I simply said I’d be there.
The next two days were torture. I didn’t know what to expect, and I was nervous, excited, anxious and a little scared. Was Mr. Holt still mad at me? Was Mrs. Holt mad at me? Was this a simple babysitting job? Did Mr. Holt expect more than just babysitting? All these thoughts and emotions circled in my brain, turning me into a nervous wreck. Luckily, my parents were too busy to notice and I avoided any contact with my friends.
Finally, Saturday was here. The first thing I did when I woke up was to grab my dick and start stroking it. I tried to concentrate on Andrea Martin, the cute blonde with a great ass in my History class. But my thoughts kept going back to Mr. Holt’s cock and me sucking it. As much as I tried to imagine Andrea sucking my cock, the visual image of me sucking Mr. Holt kept taking over my thoughts. When I finally blew my load, I was thinking about Mr. Holt blowing his load in my mouth.
It was 2:50pm and I said goodbye to my parents as I walked out the door. I made the walk down the street and found myself at the Holt’s doorstep right at 3pm. I noticed Mr. Holt’s car wasn’t in the driveway, which was a big relief. Him not being home meant I didn’t have to face him if he was still angry, and also meant this was just a normal babysitting gig. So yes, a part of me was relieved, but the part of me that had jerked off to his cock in my mouth that morning was disappointed.
I rang the doorbell, and Mrs. Holt answered and ushered me in. She was dressed in tight shorts that accented her curves and a loose tank top that allowed me to see she wasn’t wearing a bra. I had never seen her dressed like this; she was always wearing modest clothes that hid her figure. I couldn’t help but stare, and Mrs. Holt picked up on that quickly.
“My husband is out golfing; he won’t be home until 5pm. He would be upset if he knew I was dressed like this, so please don’t say anything.”
“I promise I won’t say anything,” I told her. Then added, “If you aren’t leaving until 5pm, why did you have me come over early?” My brain was racing and I was hoping she had invited me over to fuck her. Maybe she was mad at her husband and she was going to fuck me for revenge? My dick got hard in the two seconds it took for these thoughts to go thru my brain.
She looked down at my hard cock, and she got a weird look in her eye. It was if she knew what I was thinking, and knew I was going to be disappointed with what she was going to tell me.
“My husband wants me to get you ready for the evening. I’m taking the kids to my mother’s tonight. It’ll be just the two of you here tonight.”
She said this with an apologetic look in her eye and reflection in her voice. I didn’t know what to say. I had gone from the jubilation of being ready to have sex with a woman for the first time to the fear of being alone with Mr. Holt. As fast as that fear hit me, it was replaced with the excitement and anticipation of being alone with Mr. Holt and his cock.
Mrs. Holt said we had a lot to do, and we had to be ready promptly at pm, else suffer the wrath of her husband. She led me upstairs to their bedroom. When we entered, I saw an outfit laid out on the bed. My eyes immediately went to the bright pink g-string panties and matching bra. A black leather miniskirt, black lace camisole top, and black thigh-high stockings.
“Is that for me?” I stammered.
Mrs. Holt explained it was, but we had work to do before I could put them on. She led me to the bathroom and told me to get naked. She saw me hesitate, but told me we didn’t have time to waste and we didn’t want to upset her husband. The thought of him being angry killed any modesty I had and I stripped down. She handed me a razor and told me to get in the shower and to shave my public hair. I didn’t have much body hair, nothing on my chest and very little on my legs. I shaved the little public hair I had, and then shaved my legs for good measure. I thought I was done, but Mrs. Holt took the razor from my hand and told me to turn around.
“Bend over and spread your cheeks, I need to make sure you don’t have any hair near your hole.”
It felt surreal, I was bent over in the shower spreading my ass cheeks while this woman was shaving my asshole, but here I was. She made quick work of it and then told me to shower, making sure to clean everything really well.
I got out of the shower and dried myself off. Mrs. Holt had a bottle of lotion. She told me Mr. Holt loved the smell and that I needed to put it all over my body. I took the lotion and lathered it on my legs, arms and chest. I was struggling to put it on my back so Mrs. Holt took the bottle from me. She poured some lotion into her hands and started rubbing it on my back. Her soft hands felt great, and the intimate moment we were sharing brought my cock to full mast. She had put more lotion on her hands and was now rubbing it on my ass. My dick was throbbing when she told me to spread my legs. I didn’t know why, but did it anyway. She then took her lotion-covered finger and ran it between my cheeks and around my asshole. It seemed like she lingered around my hole, and the pressure of her finger on my hole was making my cock pulse.
“You didn’t put any lotion on your cock or balls. Do you want to do that or want me to take care of it?”
I couldn’t believe what I just heard her say. I couldn’t answer, my brain short-circuited. She took my silence to mean she should do it. She put lotion on her hand and got in front of me. She dropped to her knees, her mouth inches from my rock-hard dick. She reached out and ran her lotion-covered palm down my shaft and to my balls. Her hand massaged the lotion into my ball sack, cradling it as she rubbed the lotion in. She softly moved her hand to my dick and began to grip it and move her hand up and down. After two strokes I thought I was going to cum. She must have sensed it as she stopped, got up, and shyly said “I guess we should stop.”
Mrs. Holt opened the medicine cabinet and pulled out a small bottle.
“Bend over the vanity, we need to get you lubed up, it’ll make things easier later.”
I knew what she was talking about as I remembered Mr. Holt using lube before he fucked me. I bent over the vanity and stuck my ass out. Mrs. Holt applied lube to her finger and gently massaged it in and out of my hole. It felt amazing, and since only my chest was on the vanity, my cock was free to get hard again. Mrs. Holt added a second finger and I jumped a bit from the discomfort.
“Here, this will help until you get used to it” she said at the same time she reached around and grabbed my dick.
She was stroking my cock and working her fingers in and out of my hole. She was getting it lubed; getting it ready for her husband. I was feeling a buildup and knew I would cum soon. Again, she must have sensed it and stopped. She told me we needed to do my make-up.
I sat down in front of Mrs. Holt’s make-up dresser and she went to work. It took about 30 minutes for her to use concealer, foundation, blush, eye shadow, mascara, and finally a bright shade of red lipstick. She then went to her closet and pulled out a blonde wig. She attached the wig to me and stepped back. We both looked in the mirror and saw a stunning blonde young woman looking back at us. The transformation was incredible. Andrea Martin from History class had nothing on me.
It was finally time to get my outfit on. We started with the bra and panties. Both were snug but fit. Next was the skirt and camisole, and finally the thigh high stockings. My cock had remained hard throughout the make up and getting dressed. I didn’t know it was possible to have an erection for that long. As we looked at me in the full length mirror, we both admired how pretty I looked.
Suddenly Mrs. Holt gasped and said “I forgot your cage, we need to get that on.” She pulled a pink chastity cage out of a drawer and walked over to me. She pulled up my skirt revealing my erection jutting out of the panties.
“You’re going to need to take care of that before we can put this on you.” As she finished her sentence, we heard a car pull in the driveway.
“Oh my God, it’s Mr. Holt, what are we going to do? I’m not ready!” I had panic in my voice, but my dick remained hard.
Mrs. Holt grabbed my cock and started jerking it. The feeling was a 1000 times better than when I did it myself. I was going to cum quickly.
“I’m going to cum, I don’t want to get it on my clothes, where should I shoot it?”
Mrs. Holt was more panicked than I was, but she knew what to do. She dropped to her knees and put her mouth over the top of my dick. I felt her warm lips on my cock and felt her tongue flick the glands at the top of dick. She stroked one more time, and my dick erupted into her mouth. She stroked my cock as I shot load after load into her mouth. She was milking every last drop out it, swallowing all of my load. It was the greatest feeling of my life. Finally, she stopped, got up, and told me to sit on the bed.
I sat down and she put my now soft dick into the cage. She locked it with a key and explained how I could still pee, but not get hard. Just then we heard Mr. Holt yell up the stairs “You better be ready!”
“We are coming down now, honey!” Mrs. Holt replied, fear in her voice.
Mr. Holt barked back, “Tell that little slut to wait for me in the bedroom, you grab the kids and get your pathetic ass to your mom’s house.”
Mrs. Holt turned to me and whispered, “What just happened has to be our secret.”
I nodded and she left to gather the kids. In my head, I was in love with Mrs. Holt, and wanted to stay with her and fuck like newlyweds. But now Mr. Holt was home, and he clearly had other ideas. The thought of what might happen made my cock stir, and I learned what it meant to be caged when my cock couldn’t get hard.
I was scared of what was going to happen next, but deep down I wanted it…
