I felt like my entire body was buzzing as started getting ready for my babysitting job later that evening. I was excited, scared, and turned on all at the same time.
I had no idea what might be waiting for me in Steve’s secret movie stash, and his warning about doing more naughty things to me had given me plenty of self-pleasuring fantasy material all week.
I kept replaying the events from our last encounter in my head, getting more turned on by the minute. I couldn’t help but wonder how far it would go this time. Would I lose my virginity? Was I ready for that?
I wasn’t saving it for any special reason. I just hadn’t had a good reason to go any farther with anyone—yet.
I chose my outfit carefully, knowing Steve liked my tank tops and short skirts.
I picked a thin white top and a pretty bra that showed off my ample chest. Then I slipped into a short gray-and-black plaid skirt—not too short, since I was still babysitting and needed to be functional.
After a quick mirror check, I noticed that you could just see my butt and the edge of my little white thong when I bent over, but standing up, it looked perfectly fine. I was ready to go!
Ready to Earn Another Good Tip
I couldn’t even wait for 6PM to arrive, so I decided to head over a little early. As I pulled in the driveway at 5:45, I noticed only one car.
I knew that meant that Steve’s wife, Barbara, was traveling for work. This was really going to happen!
I was so excited when I knocked on the door that I could feel my nipples getting hard. I knew Steve would be able to see them through the thin material.
When Steve opened the door and grinned ear to ear, I knew he could definitely see them, and liked what he saw.
“Raven! Always a pleasure to see you,” he said, openly staring at my chest. “Carly is still up, so she’ll need dinner and a bath. I should be back home by 9 p.m.”
“Okay, thanks, Mr. H. I’ll make sure she’s well taken care of and tucked into bed by bedtime,” I replied, trying to sound casual—even though he looked like he was ready to eat me up, and I really, really wanted him to.
He grabbed his keys and started to walk out the door, then stopped and turned around.
“Oh, and Raven, be sure not to go looking for things you might not be ready to find. You know what the punishment is.” He winked as he said it, and I knew I was blushing furiously as I felt myself getting wet.
“I’ll be sure to keep that in mind,” I said, with a nervous shake in my voice.
He just laughed a little as he closed the door and left for poker night with the guys.
It was torture just trying to get through a normal night of babysitting! I could barely get the kid into bed fast enough. All I could think about was getting a chance to go see what Steve kept in his dresser.
When she finally fell asleep, I quietly crept into Steve and Barbara’s room, ready to look everywhere until I found my prize.
An Eye-Opening Stash
Steve did not make it hard to find!
I hit the jackpot when I opened the lower drawer of his dresser. It was filled with porn videos, lube and even a few interesting-looking toys.
I had never even seen a real porno before, so I had no idea they would be so hardcore. The closest thing had been late-night softcore movies on HBO and Cinemax- or Skinemax, as we used to call it back in the day. I was pretty sure these videos were going to be way more explicit than Lady Chatterley’s Lover!
And looking through those titles, it seemed Steve was into some kinky stuff I’d never even thought of.
Back Door Beauties Vol. 3, The Adventures of Buttman, Taboo 2, Bad School Girls…there were so many I wasn’t sure where to start. The bulk of the collection was centered on anal adventures and naughty schoolgirls, so he definitely had a thing for that.
Of course, it made me think of last time, when he put his thumb just barely in my butt. Was he going to want more? Did I want more?
I figured there was only one way to find out, and picked out one called Anal Angels, since the girl on the cover resembled me, with long dark wavy hair.
I brought the movie downstairs, popped it into the VHS player and turned the volume down way low.
The movie started with a classroom full of girls and a male teacher. The girl with the dark hair was being very disruptive, and the teacher told her she’d need to stay after class.
Things quickly heated up to where she was getting a bare-assed spanking by the teacher. She kept wiggling her butt and moaning, and when the teacher started fingering her, she started backing up into his fingers demanding he go harder.
All this brought back my own similar experience with Steve, except this girl on screen was way more into it and obviously more experienced than my own timid reaction had been.
When the teacher leaned over and stuck his tongue right in her butthole, my eyes about popped out of my head.
He alternated with his fingers and tongue until she came, and I rubbed myself until I was spent just watching that one scene.
I was just relaxing back on the couch, watching the on-screen action continue while lightly rubbing myself, when I heard the click of the door opening behind me.
Caught Again!
“Oh Raven, you naughty, naughty girl,” Steve said as he walked up behind me.
I was practically holding my breath as I watched the student on screen kneel down between the teacher’s legs and start giving him a blow job. I was a bit relieved. At least I knew how to do that!
Steve walked up behind me and put his hands on my shoulders first. Then, when he saw me relax and tilt my head back, he slowly ran his hands down my arms.
It was like little tingles everywhere he was touching.
“I see you found my favorite movie. You know what this means, don’t you? Tell me you want me to keep going,” Steve said as he brought his hands up to my shoulders and started to slide the little straps of my top and my bra down at the same time.
“Yessssss,” I breathed back at him with my eyes closed.
He began to slowly kiss my neck, which is something I still love to this day.
I felt the air hit my chest, and I knew my boobs were fully exposed. His hands followed quickly, gently cupping each breast and lightly stroking my nipples. I’d never felt them be so sensitive and responsive. I nearly bucked off the couch wanting to be touched everywhere.
Steve was working his way up my neck and began to kiss me, and damn was he a good kisser. Luckily, that was something I’d had a lot of practice with already, and I kissed him back with everything I had.
He broke away from the kiss to give me a stern look and said, “First, you’ll need to be punished,” as he gave each nipple a sudden painful pinch.
I yelped in surprise and opened my eyes. He was looking over me with a very naughty expression.
“Stand up, take off your panties, and bend over the couch,” Steve commanded. “I want you to be able to keep watching my favorite girl. She’s always reminded me of you.” (I knew it!)
The woman on screen was still enthusiastically blowing her teacher, taking it all the way down her throat. I was wondering if I could do something like that, or if it would make me gag.
I stood up, removed my thong, walked to the back of the couch, and bent over it.
“Spread your legs a little,” Steve instructed. “I want to get a good look at your pretty little pussy while I punish you for snooping in my things.”
I was a little shocked by the way Steve was speaking to me, but I did as I was told and bent over, knowing full well how dripping wet I was. He spread me wide and took a good look, while I blushed and hoped he liked what he saw.
He was still holding me wide open, and I felt his breath on my butt before his tongue landed on my clit and he did a very slow lick all the way up to my ass. In my head, I just kept thinking about what I had just seen on the video. I felt I knew where this was going, or at least, where I hoped it was going.
Steve did not disappoint as he continued this slow licking, all the way from the bottom, to the very top, only pausing to dip his tongue deeply into both my holes. It was driving me absolutely crazy with lust.
And even though he’s spanked me before, I still wasn’t expecting the hard smack when he suddenly stopped licking and firmly landed one hand on my ass cheek.
“Ow!” I squealed. Pretty sure that was going to leave a mark.
Just as I thought that, I heard Steve mutter how nice and bright red his handprint looked on my skin.
“Shhhh, we don’t want to wake up Carly!” Steve warned me, as he continued to smack my ass while occasionally stopping to slide his fingers up and down my wetness while admiring his handiwork.
When he started to not just slide, but slip his finger in and out, deeper every time, after every spank, that’s when I really started to squirm. I couldn’t help but let out a little moan when he added two, then three fingers.
I started craving the spankings because of what followed.
“Just beautiful. So wet and needy,” Steve whispered as he slowly pumped his fingers in and out while giving my clit some much-needed attention. “Are you ready to show me what you learned last time?” he asked as he walked around to the front of the couch. He was so hard he looked ready to pop out of his jeans.
I didn’t answer, and when he unzipped his pants, I just looked up and opened my mouth to show him I was ready. I placed both hands down on the couch cushions to prop myself up, and he easily slid right in my mouth.
“Oh, that feels so good,” Steve groaned as he pumped my mouth. “Keep sucking just like last time. Try using your tongue a little more.”
He fisted my hair in his hands and began guiding my head to the rhythm he wanted. He went deeper this time, and when I gagged slightly, he eased back and slowed his pace.
I thought I was getting pretty good at this, and took time to use my tongue, swirling around his head like the girl in the video had done. I also ran my tongue up under the rim and moved it around as I was sucking him. That video was very educational!
Just as I thought he was ready to come, he pulled out.
Not So Fast
“Oh no, I don’t want to be done with you yet,” he said, a little out of breath. “I want you to stay just like that. I like you bent over. But before we go any farther, I need to know, are you a virgin?”
I was a bit embarrassed at the question, but knew I needed to be honest.
“Yes,” I answered, knowing I sounded a bit unsure of myself. “But I want to… try more things,” I added. I didn’t want him to have second thoughts and stop.
I had heard that it was supposed to hurt a bit the first time, but at my age I’d already been using tampons for years and his fingers had felt damn good so I didn’t expect it to be a big deal.
“My mom put me on the pill when I turned sixteen, so we don’t need to worry about that either,” I mentioned, thinking that would really sweeten the deal.
As Steve moved back around the back side of the couch, I got a clear view of the TV again, and the student was bent over the desk and getting railed by her teacher’s enormous dick.
Steve actually measured up quite well, but not as big as that guy. His size was the only thing that made me pause. I hadn’t exactly had anything that BIG in me before.
I felt Steve move up behind me, and reach around me to start fondling my nipples again, tugging them a little. I really loved that.
“Next time, I’d like to spend some time sucking on these beauties,” he said, as I felt him rubbing his dick up and down my slit, getting covered in my wetness.
“I’ll go slow,” Steve said, as he started to slip himself into me.
I felt just the head go in, along with a couple of inches, stretching me a little more than his fingers had before. I moaned a little and tried pressing back to encourage him to continue.
“Oh fuck, this is so hot, I can’t believe this is happening,” Steve spoke the words aloud, like he was speaking what was in my own head.
When he finally pushed all the way in, I did feel a pinch, much like the first time he’d used his fingers, but farther up.
And this time, I felt so full, I just gasped a bit and bent over a bit more onto my forearms. The couch was just the right height to keep my ass in the air and me fairly comfortable at the same time.
Steve started to moving faster once he was sure I was ok. And as he pounded a bit harder, faster, and deeper, he started to hit spot somewhere deep inside that I had never felt before.
It was different from the orgasms I gave myself, and was coming from the inside rather than being centered on my clit on the outside.
At this point, the action on the screen had taken quite a turn, and the teacher was working his monster cock into the naughty schoolgirl’s asshole. I had never seen anything like that before, and the rush of wetness from that scene must have been noticeable to Steve because he asked me, “You like what you’re seeing, naughty girl?”
I felt caught all over again! How could I be liking something so pervy? Did people actually do this stuff in real life? Did Steve want to do that to me?
“Looks like she’s enjoying herself,” I said.
“I don’t think your tight little butt is ready for that yet, but we can work up to it,” he said as he slid out of me and slipped his thumb in my pussy, getting it good and wet.
I wasn’t sure what he was doing until he started fucking me again and smoothly slipped his thumb into my butt. And it wasn’t just a little tease this time. He put it all the way in to the top, and spread his fingers out over my back.
“Oh, fuck!” I squealed as quietly as possible. It actually hurt a little at first, but then it started feeling pretty good. I think the naughtiness of it had me extra turned on.
It felt like he was using that hand on my back, with the thumb in my butt, to guide my body back and forth on his dick. The sensations from that, the feelings from deep inside, and the visuals of the man on screen pulling out and coming in the student’s mouth set something loose inside me. My legs started to tremble, and I nearly screamed as I came.
My reaction set off Steve as well, and I heard a guttural noise behind me as he slammed in as far as he could go, both with his dick and that thumb buried in my asshole.
I felt his hot cum spurt inside me, which was a unique and satisfying feeling, to be filled so deep inside. It was hotter than I expected it to be, and I was surprised how much of it there was.
He removed his thumb and nearly collapsed over my back, softening inside of me. We both quietly watched the screen, trying to catch our breath while he did a few slow pumps, making his cum slowly ooze out and slide down my leg.
The porn girl had let the teacher spurt in her mouth and all over her face and boobs. She was now wiping it off her body with her hands and licking it off her fingers.
I felt Steve slide his hand all the way up my leg, and I knew what was coming next.
He brought his hand to my mouth, and I instinctively opened it, licking off his cum and sucking it off his fingers, just like the girl in the video.
“Mmmmmm, so good,” I said because that’s what she had said, and I was a quick learner. He went back a couple more times, wiping more and more as it dripped out of me, and I cleaned him off each time.
After I finished sucking his fingers clean, Steve pulled out and wiped us both off with a blanket from the couch.
“Going to have to do some laundry,” he laughed as he tossed the blanket in the corner.
“You’ve definitely earned another good tip for tonight. You just might be the best babysitter in the whole neighborhood!” Steve said with a huge grin. “Get dressed but don’t leave yet, I have a present for you.”
As Steve went to his bedroom, I pulled my shirt back up and put back on my thong. I think Steve had enjoyed leaving my skirt on.
He came back in with a little box I had seen in the drawer with the videos.
“I got this for my wife, but she never wanted to use it,” he said as he opened the box. “I think you may be the perfect one to try it out.”
Inside was something that looked like a small bulb, with a slender neck and a little pink jewel at the end of a flared base.
“What is that?” I asked, incredibly curious about what I was supposed to do with it.
“I want you to take this home and practice wearing it. It’s called a butt plug. From your reactions tonight, I think you’ll enjoy it. And here’s some lube to help you out,” he said as he handed me the box and a little tube of lube.
“If you really want to try more of the things from my videos, I want you to wear it next time you babysit. If I see that little jewel in your butt, I’ll know you’re ready to play,” he said with a wink and very naughty smile.
“OK, I’ll think about it,” I replied with my own naughty smile, knowing I would probably do more than just think.
I could hardly wait until next week…
