I was incredibly excited to try out Steve’s gift, and practiced with the butt plug all week, getting used to the feeling of it sliding in and out, wondering what Steve would feel like inside me compared to the small plug.
I got dressed in what was becoming my “babysitting uniform” of sorts, as I knew Steve loved my short little skirts and low-cut tank tops that showed off my curves.
I slid the plug in easily, after all my practice, and checked myself out in the mirror. You could just see the sparkle of the pink jewel hidden behind my white thong. I knew Steve would see it and know I was ready to “play,” as he put it.
When I got to Steve and Barb’s house, I saw a lot more cars in the driveway than normal and wondered what was going on. I knew Barb was still out of town, and I assumed Steve was headed to his usual game night. Steve opened the door with a big smile, obviously happy to see me, which gave me a little thrill.
“Hey, Raven! Always a delight to see you,” Steve said, wearing a mischievous look. “Since Barb is out of town, the guys decided to have game night at my place. Hope you don’t mind—it’ll be the usual babysitting job. But I was hoping you could stick around a little longer and help with the party. I’ll pay you extra, of course, for the additional time. It’ll be really easy—just getting us some drinks, keeping the chip bowls filled, that sort of thing.”
I didn’t have to be home until 11:30, and I wanted to make sure we had some alone time, so I was willing to wait until they finished their game.
“Sure, Mr. H, I can totally do that!” I told him with a big smile.
“OK, great, come on in and meet the guys,” Steve said as he stepped into the hallway and let me in the door.
I walked in to see four men sitting around Steve’s dining room table, with a Yahtzee game in the center. Steve introduced me to Greg, Brian, Carl, and Josh. I recognized a couple of other neighborhood dads. “Carly is upstairs. Why don’t you go take care of her for a bit and come downstairs when she is in bed?”
“OK, Mr. H,” I said and turned to head upstairs. “Oh, wait!” Steve said suddenly, and I stopped to turn around. “Raven, that outfit looks so good on you tonight. Can you give a little twirl and show the guys what you’re wearing?”
A twirl? That was going to lift up my skirt, and they’d all be able to see my butt and the little pink jewel poking out of it! Before I had time to think too much about it and chicken out, I gave a playful little twirl and turned around to see a tableful of very lustful faces staring back.
I knew they had seen it. I started to wonder how much Steve had already told them. The thought that he was sharing the intimate things we did made me feel a little embarrassed—but also turned on. What in the world did he have planned for me tonight? I wondered.
“I told you guys what an amazing babysitter she is, right? Raven’s offered to help out with the party and keep us happy tonight. Isn’t that right, Raven?” he asked with a wink.
“Yes, I’m happy to stick around for a little bit longer tonight,” I said before I ran upstairs, heart racing, all kinds of naughty thoughts running through my head about the table of men downstairs.
They were all between the ages of 30 and 50, handsome, a few silver fox types. I could barely stop from rubbing myself just thinking about what it’s going to be like helping them out later.
His little girl Carly was in quite a mood that night, and it took me longer than usual to get her into bed. By the time I made it back downstairs, the guys had been drinking for a bit and were getting pretty rowdy. I noticed the TV had another one of Steve’s porn movies on it, and he must’ve seen the surprised expression on my face when I saw what was playing. It was some kind of gangbang scene with his favorite porn actress with the long dark hair that looks like mine.
“Oh, Raven, I hope you don’t mind. We usually have stag films playing during game night. It’s a guy thing,” he explained. “Don’t worry, I know you didn’t pick this one out, ha-ha,” he said with a little smirk. “Greg and Brian could use a refill on their drinks. It’s pretty easy. They’re having rum and Coke and a beer. Just grab it from the kitchen.”
“OK, I can do that,” I said as I headed into the kitchen, trying to calm my racing heart. I was feeling a bit nervous, but these were just neighborhood dads… I’m sure it would be OK. I think I was more worried about what I might do than what they might try.
I brought the drinks to the table and set them down in front of Greg and Brian. I bent down low, and knew the men across the table got a great view down my top. I’d worn a push-up bra that night, and I knew my 34DDs were looking pretty spectacular.
I kept up with their drinks and snacks for a bit. They were all very polite at first, but the more they drank, the more touchy-feely they were getting. I knew I’d felt a hand on my thigh, and I was pretty sure Greg had grazed my nipple on purpose the last time I brought him a drink. As a result, both nipples were standing at attention.
After about an hour, Brian eyed my obviously hard nipples and said, “Hey, Raven, I need some extra luck. Why don’t you come over here and sit on my lap for a minute? You can blow on my dice. We hear you’re pretty good at…blowing.”
At hearing that, I was pretty sure Steve must have told them everything! I started blushing as I walked over to Brian and gently sat in his lap. He put his hand high up on my thigh and held out his dice.
As I leaned over to blow on the dice, I felt his dick getting hard beneath me. Something about it made me want to get it even harder, so I gave his dice a sexy, slow blow, then smiled innocently and told the group, “I’m happy to give you all a blow if you need a little luck.”
I loved the shocked way the men’s mouths fell open after I said that, and I gave my butt a little wiggle on Brian’s lap. I was enjoying feeling the combination of the butt plug pressing into me and Brian’s dick getting even harder.
It was a pretty impressive lump under me, and I started getting wetter thinking about how big his dick must be. I was a bit worried there would be a big wet spot on his pants when I stood up.
“Oh, I see Mike needs a refill!” I said as I stood up quickly before things got too heated. “I’ll take care of that!”
I couldn’t believe Brian had put his hand so far up my leg, and that he’d gotten so hard from it. I’d babysat for his family once before, and he’d never made any moves or even looked at me in “that way.”
I figured he was fueled with alcohol, Steve’s stories, and the porn playing in the background. I noticed it was getting more and more explicit, with the actress getting every hole filled and then some.
I saw the men keep looking over at the movie every once in a while, and I was sure it was filling their heads with dirty thoughts about me. I couldn’t get over how much the girl looked like me.
When I came back in, Steve said, “OK, it’s my turn now! I need a little of that luck!” and patted his lap.
I went to sit on Steve’s lap, and immediately felt his hand slide up my thigh just like Brian’s had done.
“Now blow me, oops, I mean these, like a good girl,” he said with a laugh as he shook his dice in front of me.
I leaned over, licked my lips, and gave them a sexy blow. He threw the dice and cheered when he rolled a full house.
“Damn, Raven, you are good luck!” he shouted, as I felt his hand slide all the way up and test my wetness. I leaned forward a little, letting him know I didn’t mind what he was doing.
I tried not to let it show on my face when he started fingering me under the table while the other four men looked on. I knew my face was getting flushed, and my breathing heavier, and I started thinking it might be obvious what Steve was doing to me in front of everyone.
“You know,” said Steve, I bet all of the guys could use a little of your luck. Why don’t you flash us those beautiful titties you’ve been teasing all night?” I could tell Steve had had a lot to drink by now and was feeling bolder. I saw the rapt attention of every man at the table, and it was really turning me on. I felt like I was feeding on their lust and attention as they stared at me expectantly.
I giggled shyly, pulled one strap down, and let my nipple peek out before pulling it back up.
“Oh, no. Not just a tease. We want to see the whole thing! Let these men have a look at your beautiful body,” Steve said as he put his hands on my shoulders and slid my top and bra straps down.
My breasts were already so pushed up by the bra that they nearly toppled out of my top as it came down to my waist, exposing me completely. My nipples immediately hardened, and I didn’t think I could get any wetter at this point, until Steve gave each nipple a hard little pinch.
I was pretty sure I was going to need to pick their jaws up off the floor, and then suddenly, the guys burst out with whoops and whistles. “Give us a little shake!” one of them yelled. “Just a little jiggle!”
I indulged their request and gave them a little jiggle and smile. I was loving their attention.
“Now this is a party!” Carl said as he clapped. “We need to have game night at Steve’s every week!”
I laughed as I pulled my top back up. “It’s getting late, so that’s all you rowdy boys get for tonight,” I said with a naughty look, and a couple of them jokingly booed. I needed to be home in an hour, and I couldn’t wait to get Steve alone after being so turned on.
“It’s been an amazing game night, Steve, and thanks for the extra treat, Raven,” Josh said as they all stood to leave. “Make sure Steve takes good care of you after we leave,” he said with a wink as they all filed out the door.
Finally! They were alone!
“Sorry about the guys, they can get kind of rowdy on these game nights. I hope you didn’t mind,” Steve said a little sheepishly.
“No, not at all,” I said. “The guys were really nice. Maybe a little handsy, but nothing I couldn’t handle.”
“Oh, really? And did you enjoy… being handled?” Steve asked with a sexy smirk. “I hope you’d be willing to help us out at game night again and maybe even ‘handle you’ a little more next time.”
“I’d like that if you would enjoy it too,” I said, surprising myself with my eagerness to please him.
“I think that sounds like a lovely idea. But you know what’s even better? Why don’t you turn around, bend over, and show me how well my little gift fits?” Steve said in a very commanding tone that I immediately felt compelled to obey.
I giggled as I bent over and shook my ass at him, so the little jewel would catch the light and twinkle.
“Have you been wearing it every night?” he asked.
“Yes,” I said. “I’ve even used it when I’m pleasuring myself. I wanted to be ready for you.”
“Oh, I think you’re ready to play, but let’s get you warmed up first,” Steve said, as he got on his knees, moved my thong aside, and gave me a slow, sensual lick. I felt him grab a hold of the little jewel sticking out of my butt with his teeth and tug back and push forward and then tug back and push forward again. I sighed at the pleasure it was causing to pulse through my body.
“I want you right here, but get on all fours. Put that little butt of yours up in the air and your face on the floor. And take those panties off. I don’t want anything in my way,” Steve commanded.
I got into position, eagerly awaiting whatever would happen next. I felt him start to twist the butt plug. First right, then left, making every little sensation count. I started moving my hips a little. I wanted him to increase the pressure and the tempo. I wanted to come so bad.
“Oh no,” he said, “You’re not coming that easily. We’re making this last a little longer.” He then pulled the plug all the way out and pushed it back in.
He did this a few more times, teasing me, licking me, and finally he went in for the kill and sucked my clit into his mouth, as he slowly pulled out the plug, and I came with a long moan of pure pleasure.
“You stay right there,” he said as he crawled over to my face on his hands and knees and sat down on the floor by my head. I saw all 10” of his thick cock sticking up from his lap, hard and ready, and knew he wanted me to blow him a little bit before we moved on. I raised up on my elbows and sucked him into my mouth in one smooth motion.
“Just like that, Raven, you’re so good at this now. Make sure you get it really good and wet. You did a really good job with your butt plug, but we can’t have too much lube for what I have planned next.”
I gave him a wetter and sloppier blowjob than usual, making sure it was good and dripping by the time he pulled away.
“OK, are you ready for this?” he asked.
“I’m all yours,” I said as I reached back to spread my ass, completely exposing everything to him. I was obviously dripping with excitement, so I wasn’t surprised when he plunged into my wet and waiting pussy first.
“Oh, you always feel so hot and tight, Raven,” Steve said as he slowly pumped into me. “I think going into your tightest hole just might make me lose my mind.”
I heard the flip of a bottle cap and then felt the drizzle of something cool and wet on my ass crack. He withdrew from me and slid his cock up and down, coating himself in the lube. I clenched a little when I felt him zero in on the sensitive entrance to my ass.
“Just relax,” Steve said. “Once the tip goes in, it’ll get a lot easier. It’s just like the plug I gave you.”
I felt him pushing, and I felt pressure, but I was used to it from the plug, so it excited me. I pushed back a little on him, and the head of his dick popped in without much resistance. Once it was in, it was still a surprise at how much bigger and fuller it felt than the plug.
“Are you OK, baby girl?” he asked. “I’m gonna take this real slow, just a little at a time,” he said as he pushed in another inch. I wiggled my butt to show him I was ready for more, and he pulled out a little and then went another couple of inches deeper. He proceeded to do the same move, slowly getting deeper and deeper until I felt him bottom out, embedded deeply in my ass.
I couldn’t believe how different it felt from the short plug. It was an entirely new sensation. And just the thought that I had a dick deep in my ass was making me more turned on than ever.
“I’ve got another little toy for you,” he said as he rested deep inside of me, letting me get used to his size. I heard a little buzzing noise as he brought his hand around to my clit.
“It’s a vibrator. I want to make sure you get as much pleasure out of this as I am.” He started to move slowly in and out while stroking me with the vibrator.
I felt my orgasm building up quickly as he started pumping harder from behind. As we got into a good rhythm, I felt the familiar sharp smack on my ass, first one cheek and then the other. I should have expected a good spanking by then.
The vibrator on my sensitive clit, a dick in my ass, and the hard spanking made me come faster than I ever had in my life. I was almost disappointed to not enjoy it for longer!
“Oh God, that’s sexy,” I heard Steve say from behind. “This is the hottest ass I have ever had in my life,” he said as he picked up this tempo and started slamming me even harder while I rode out my post-orgasmic bliss.
“You are so sexy, Raven. The view I have back here is amazing. I don’t know how long I’m gonna last. Is it OK if I come in your ass?” he asked.
From what I’d seen in his movies, I had already assumed he would be doing that. And said, “Yes, Steve, you can come wherever you want. I’m yours to play with tonight.”
I think my words got him even more excited, and he started going faster and harder. By this point, I was pushing back to meet his thrusts each time.
He gave me one last loud spank, pushed in all the way, and came into me, hot and fast and deep. I could feel it coming out in big spurts and filling me up.
He rested inside me after that and then whispered in my ear, “I want you to hold still and clench your butt tight when I pull out. I don’t want to miss a bit of this.”
I wasn’t sure why he was asking, but I did as I was told and clinched as soon as he withdrew. Holding has cum inside me. I heard him kneel down behind me and felt him spread my ass cheeks. “Show daddy the sexy cream pie you brought for dessert,” he said.
I relaxed my butt and felt his cum start running down my leg.
“That’s it, Raven, push it out for me. Let me see how good I filled you.”
I gave a little push, and I felt more oozing out.
“Oh, that’s a beautiful sight from back here,” he said as he fingered my butthole a little bit more. I felt extra sensitive from the stretching he had just given me. “This time, I’M going to clean YOU up,” he said.
I felt his tongue on my ass and jumped a little because I hadn’t expected that. I was starting to understand that Steve had very few limits when it came to his sexual gratification.
He drove his tongue in deep, doing a very thorough job. I pushed my ass back into his face to show him how much I like his extra efforts.
He used a towel to wipe the bit that had been slowly running down my legs, only pausing to give my ass and pussy little licks in between his gentle wiping.
“You are quite a sweet little treat, Raven,” he said. “I could eat your ass all day.”
I laughed and told him I probably wouldn’t mind that at all.
“Oh, Raven, I wish I could keep you here all night and do all kinds of naughty things to you, but I know you have to get home by 11:30 so your mom doesn’t get worried. I’ve got another present for you before I leave.”
He went to his room and came back with a box like the one from last week, but this one held two items. A plug similar to the one he had already given me, but about twice the size, with a pretty purple jewel at the end. Next to that was a string of what looked like beads. These were also purple, each one about the size of a gumball.
“Oh! You got me a new present in my favorite color!” I exclaimed. “But what are the beads? Some sort of necklace?”
“Oh no, not a necklace, these are called anal beads. We’re going to have some fun with them next time. But I thought I’d let you take them home in case you wanted to try them on your own first. I want you to push each one into you and fill yourself up, and then masturbate. Slowly pull them out as you come, and you’ll come harder than ever.”
I couldn’t wait to get home and give them a try. My ass had gotten quite a workout tonight, but I felt like I was ready for more.
“I really love how eager you are to learn,” he said. “I’m going to miss you when you leave for college in the fall. Are you interested in earning extra money again at game night? It could help cover some of your school costs. You wouldn’t need to take out all of those school loans.”
“I’m interested,” I said, thinking that getting a jumpstart on paying for school sounded like a great idea.
“Brian told me tonight that he wanted to do a little more,” Steve confided, “but that I should ask you first. I told him to let me talk to you. I didn’t want you to have any surprises you weren’t ready for.”
“So, let them touch me more? Or see a little more?” I asked
“Yes, and maybe even more. This neighborhood can get quite surprising once you get to know everyone. We do a bit of wife swapping, if you know what that is, and we have some wild parties. So, everyone’s pretty open, accepting, and sharing. Brian wanted to know if I would share you with him. And then all the other guys wanted in. From what I saw tonight, I think you would enjoy the experience and all the extra attention.”
I was pretty sure Steve was right, but I didn’t want to seem too eager and was worried I was turning into a bit of a slut at this point. But I was making extra money for college, so it was all going to a good cause. And the men had all been pretty respectful of any boundaries I presented.
“You can tell them it’s OK,” I told Steve. Then I remembered how big Brian felt when I sat on his lap.
“Do they all want to do what you did tonight? Brain’s kind of bigger, if you know what I mean. It felt like I was sitting on a log.”
“Well, Raven, why do you think that new plug I gave you is so big? You’re going to need to do some practice to make sure everybody has a good time. Brian is pretty excited about getting in your tight little ass.”
My butt nearly clinched in anticipation, thinking about that giant pole going in me. But I remembered how once it got in, everything seemed to stretch and accommodate. Then I started thinking it might be pretty hot, especially with Steve watching.
“Tell the guys I can’t wait,” I said in a nervous but excited voice.
“OK, great, I’ll see you next week, and I’ll let the guys know you are coming so they can bring extra cash. Oh, and make sure you bring the beads, and wear one of your cute little outfits with the plug again. I think seeing that really got them going, which of course would mean extra tips for you. The happier and drunker they get, well, it could be quite a lucrative night for you.”
Steve walked me to the door and made sure I took my new gift with me. I walked to my car, knowing I would be speeding all the way home. I couldn’t wait to see how those beads felt and knew I would spend all week fantasizing about game night and what those sexy older men had in store for me.
