Chapter 2 of Surprise After Surprise. Day two of what would turn out to be a fantastic tour day weekend with me new girlfriend….and her family.
Day 2: Friday
Following our morning conclusion to the prior night everyone kind of filed into the kitchen, sat around the table and acted like a normal family. Casey, amongst her other freakish talents was also a great cook. Casey stood at stove cooking breakfast with a sweet and very content smile on her face and the kids were sitting at the table laughing and carrying on like kids do.. I had to stop and think, “fuck, did last night really happen”? The day went pretty normal, kids played outside, in their rooms and ran thru the house with way to much energy. Casey and I sat in the living room just talking as she poured out her life stories and was loving the fact that I was sitting there listening. The house was beautiful, in the back yard was a huge screened in pool, then outside the pool screen there was a very nice fenced in backyard with a seven foot high white vinyl fence. At one point we went outside and sat on the back patio while the kids played in the pool. Casey and I talked just sat and carried on a normal conversation, I don’t think either one of us talked about the sex once. It was closing in on 5pm, as I looked over into the pool the kids started looking a bit promiscuous and giggly. It wasn’t long before hands were roaming and ideas were flourishing. When Myra gave a little chirp to Mike, “stop it, I’m saving myself for Dan” as she looked at me and smiled. I think the girls really liked me, I wasn’t sure if they liked me for me, if they just liked my dick and sex or they were relating me to the “cool” fatherly figure. Whatever the case they certainly did enjoy having me there. Until now the day had gone on like any other normal day in a normal family, Casey and I talked and oh yeah, ffshe did mention that she was still in disbelief that I was Ok with everything. Just after 5 everyone came in and had dinner, then they all faded into he living room. When Casey and I came into the living room I was kind of surprised to see that the kids were watching a porn video. Child porn to be exact, Casey smiled and said I think they’re getting horny, It was kind of hard for me to imagine two 10yr olds and two 11 yr olds watching porn and getting horny but then I recalled back to my child hood. I fucked my cousin in an upstairs closet when we were also 10 years old so I guess I realized that they could surely have it in them. Casey cuddled with me and whispered, “can the boys play tonight, I want you to break them in too”. I smiled and replied, “what is your vision of breaking them in”?. That’s when Casey said she had been preparing the boys for this day with her vibrators and dildo’s for a long time and thought they would be ready, then she joked and laughed and said “besides your perfect for them because you don’t have a huge dick”. Guys weren’t really my thing although I had had a few encounters but two young boys with tiny little dicks, now that had my attention. When I was a kid I remember my two cousins and I would suck each other’s dicks and experiment a little. After last nights fun I was ready for round two, âwhatever it might bring. As for the boys, Mike was 11 but you could have convinced me he was 8, very small frame and young looking face, Jason at 10 years old looked 7, I assume their father was a small framed kind of skinny guy, Casey confirmed that he was kind of a smaller scrawny dude. As I looked over Mike had taken his underpants off and was gently playing with his dick while he watched 2 young boys sucking each other on the video. All I was wearing was an old pair of Casey’s husbands house shorts and a t-shirt, the shorts were loose, baggy and sloppy to the point that when I sat down my dick and balls would fall out of the sides. I started getting aroused. When Casey noticed that, she smiled and told Mike come to over to me. He walked over to where I was sitting in the Lazy Boy with his tiny little pencil thick dick sticking straight out. Casey said “take Dans dick out and play with it”, I quickly interjected and said “come here Mike, let me see what we got here”. I could tell that that really pleased Casey, knowing that I was taking control with her son. Mike walked over to me and stood at attention, I took his little cock and started rubbing it up and down between my two fingers. I asked Mike if he could cum yet, he proudly said “I think so”. I laid back in the easy chair and told Mike to climb up and stand on my thighs putting that little dick right at face level. Mike did as I told him and was smiling from ear to ear, I asked him what he thought I should do now, he looked at Casey and got the nod of approval and looked back at me and said “can you suck it”? With that I took Mike’s little prick in my mouth, his dick was only about 2-1/2” long and just barely thicker than a pencil, I was surprised at how much I enjoyed his little dick. Casey enjoyed it too, she let out a moan and stood up and practically ripped her clothes off as she walked over to us. The other three kids just sat there and watched for a bit. Casey came over and insisted on sharing Mike’s cock with me, wasn’t long before he did something, it was such a thin liquid that I wasn’t sure if he came or peed. Mike was all smiles and said “wow I liked that” Casey agreed and said she liked it to. Casey looked at Mike and said “do you still want to try it tonight”, Mike totally in the game said “yes please”. Casey told him to pull my shorts off and suck my cock which he happily did. Meanwhile the other kids were getting restless, Callie was holding Myra’s head as Myra licked her now very moist slit. Casey sat back and looked around admiringly at her two daughters, her son sucking my cock and her youngest son standing there rubbing Mike’s head as he fondled his own balls. Casey asked me if I ever thought I would be in this situation? Of course the answer was no but now that I had committed myself I was going to enjoy it. Casey stood up and ran her fingers thru her crotch, let out a big sigh and yelled “Oh Fuck I’m Glad Your here” and it was obvious that night #2 was was going to be a good one. After Mike sucked me a bit Casey asked him if he was ready to get fucked in the ass with Dan’s hard cock. Hearing her ask that fucking hot question really got me turned on. Mike got up and with out being asked went and got the massage oil out of the couch arm rest. Mike hurried back over to me and handed me the oil, he stood there smiling like I was going to give him some really great candy, I was hoping he could take the candy I was delivering. I squirted some oil on my hand and fingers and thoroughly lubed up his ass, when I slid my finger into his little ass he actually moaned and said “ooooooh I like that”. Casey asked me how I wanted to do it. “On your hands and knees Mike”, I said as slid up behind him and oiled him up a little more and then I put my dick up against his ass hole, I rubbed it there for a minute or two just to tease him and my audience. Casey was two inches from his ass staring intently and at the same time fondling his dick and balls….I moved forward just a little and pushed a little harder and then I pushed just the head of my dick in, Mike flinched a little and gave a little whine, I held firm right there and said “Mike if you change your mind and want me to stop just say something” and he quickly replied “no, I’m ready I want to try it”. With that I edged forward and pushed my rock hard cock into that little ass about 1/2 way, I paused again and told Mike when he was ready just push back on my dick. The whole time Casey was whispering to him, “that’s it baby, you got his cock in your ass, how do you like it, it’s so hot mommy is coming just from watching.” Mike pushed back and forced my whole cock deep into his ass, at that point I started moving in and out faster and faster until I was fucking this little 11yr old boy just like we had been doing it for months. This boys waist was so small that as I held him and fucked him my fingers and thumb almost touched around his waist. I got close to exploding my load into this little ass, Casey sensed it and said “Jason quick get over here” then she looked at me and said “pull out when you’re ready, I want you to squirt in Jason’s mouth”. I fucked Mike for another two minutes really slamming his ass and then pulled out, Casey grabbed Jason by the hair, (Seems she loves to pull hair) and shoved Jason’s mouth right on to my cock just as I let loose, I grabbed his head and face fucked him hard a few times and again Casey told him not to swallow it. I think Casey really got off on swapping cum. When I was done Jason stood up and with a mouth full of cum, he kissed his mom and spit it into her mouth, I knew what was coming next, Casey came to me and gave me a fucking hot hot cum filled kiss. Jason had a look on his face like he just got the greatest Christmas present in the world. The whole time I had kinda got side tracked from the girls, now Callie had Myra on all fours and was really working on her ass with her fingers and her tongue. I smiled at Casey and she told me that she had told the kids that tonight was all about our asses and everyone was going to have some ass fun. I said “me too” and she smiled and said “I hope so” and smiled again. We took a little break and all 4 kids went to the kitchen for a drink of soda. I took that opportunity to get my fingers nice and wet and gooey from fingering Casey’s hot dripping pussy and then I shared them with Casey as we both licked them clean. Casey held me tight and said “god, I love doing this with you, you’re just as freaky and kinky as I am”. After our little break it was my turn to take charge. With the massage oil in hand I looked at Jason and said “common over here Jason”, as he walked over to me I sat him on my lap, with my hard cock poking him in the Back I said “do you want a turn now”? Without the slightest hesitation he said “yes, I want to try it”. As I played with Jason’s even smaller dick I beckoned for Myra to come and help me, Myra quickly got up and came to me and with a very excited voice and a big smile she said “What Do You Want Me To Do”? I told her to give me a kiss while she plays with Jason’s little 10yr old dick. All in one motion she gave me her little tender mouth and grabbed Jason’s dick and started jerking it. After I experienced her excellent kissing for a couple of minutes I lifted Jason off of my lap and told both Myra and Jason to suck my dick and get it nice and wet. It’s hard to tell this story and keep it to just one event, Callie, Mike and Casey were all keeping busy right next to us as I prepared to put my rock hard cock into that little ass of Jason’s. As Myra and Jason were working on my cock I fingered Jason’s little asshole a bit. I paused and said “Jason, I’m not sure my cock will fit in here” as I pushed my finger in a little further. As soon as I said that, Myra jumped up and ran to the couch, opened the arm rest and came back with one of the family dildos, with a happy smile on her face she said “this fits, it looks as big as yours”. I think she was right. I lubed my hand and fingers up and continued to finger his ass some more, I poured some oil on my cock and smiled at Jason and said “comon buddy let’s do this”. I pulled him backwards to me and pulled him up on my lap. As I did with Mike I slid my cock ever so slightly forward, after some playing and rubbing my dick on his asshole I pushed the head in. Jason looked at me and said “it doesn’t hurt to bad I kind of like it” so with that being said I went in further and further until I was buried 6” deep. I reached around and played with his dick while I fucked him and ethen I pulled Myra’s head down on his cock. Casey beamed with pride and said “look at that Jason you’re getting a double treat”. I stood up still holding Jason’s little 50 or 60lb body as I maneuvered him around so I was no pumping him from behind. When I was getting close I asked Casey who she wanted to take this load, Callie was the winner, she came over and waited with her mouth wide open waiting for me to fill her mouth up with my cum. Kneeling there fucking this 10yr old boys tight ass and staring down at Callie kneeling down next to me with her mouth wide open was like being in the “Freaky Sex Worlds Hall of Fame” I pulled out and shoved my cook into Callie’s mouth and then we went through the whole cum swapping scene again only this time Casey seem to really get into smearing the hot cum all over our mouths and faces, licking and kissing it all off. After my second orgasm it was time for a little break again. While they gave me time to get hard again I Watching Casey and the Kids doing everything thinkable (and even unthinkable), it was such a turn on that it didn’t take me very long to get rock hard again. Casey was kneeling up to the couch and had Callie laying on her back, Casey was eating Callie’s pussy vigorously and then she stuck her tongue out, curled it and rammed it into Callie’s pussy, tongue fucking her hard and sloppy. Casey moved over and grabbed Myra (by the hair of course) and barked on order: “finger fuck your sister and get them nice and wet, I want you to smear it all over my face”. Myra fingered her sister with 2 fingers and kept pulling them out of Callie’s pussy and wiping them on Casey face. Casey came over and stroked my cock and said “how you feeling baby, do you wanna lick my face clean and taste Callie’s sweet little pussy, don’t forget you got two more virgin asses to go” and with a short pause she added “and one experienced ass”. Feeling even more in charge now I stood up in the middle of the floor and said “ok everyone over here, who wants to get busy on my cock”. These kids really did seem to like the sex and the kink, they all came over and started playing with and sucking my cock with really freaky little Myra working her finger in and out of my ass. I looked at Casey and nodded toward my cock and said “what, are you so special you don’t need to help ‘em out”? Casey excepted my challenge and moved in behind me and with her fingers and tongue started working on my asshole and instructing Myra on how to pleasure my asshole. I had everyone pause while I laid on the floor, jokingly I said OK everyone back to work, except for you Myra, I want you to squat on my face so that I can eat your juicy little pussy. I really got into eating and sucking Myra’s pussy, When I was ready I said in a quiet voice “OK girls who wants to be first”? LOL, these girls aren’t shy, they both spoke up right away and said “MEEEE”. I asked the boys if they were doing ok after getting their ass cherry popped and were both all smiles. Just for fun I made Callie and Myra do Rock Paper Scissors to see who was first. Myra was the winner. Looking at her tiny little frame I couldn’t believe my luck knowing that in a few minutes I was going to stick my cock in this 10yr old ass, an ass that barely filled up the palms of my hand. Wanting to be very gentle I took Myra to couch and laid her down. I took the oil and again doused my had and fingers, as I stared into her little eyes, I began caressing her ass and asshole, I slowly slid my finger in and out of Myra’s ass. Myra was really getting in to it, I went up to two fingers. Myra’s little eyes were glistening and rolling as I fingered her ass, Callie came over with the dildo and edged it up to her asshole and said “let’s use this”. I pulled my hand back and let Callie slide the dildo into her ass, it was very obvious that these two girls had practiced this before. “Be careful I said and Callie reassured me she had done this before. Watching Callie slowly insert that dildo and seeing it slide in past Myra’s asshole was such a turn on I almost shot my load right there. Myra didn’t seem to have any problem at all taking that dildo. I looked over and Casey was having fun with the boys but staring a lazer gaze at me and Myra. While Callie was fucking her sister with the dildo she leaned over to me and started kissing me, man that 11yr old girl could kiss with the best of them. Casey left the boys and once again positioned herself 5 inches away from Myra’s ass where she stared like she couldn’t wait to get at it. After a few minutes more of dildo action Callie pulled it out and promptly stuck it in my mouth. God these kids were sexual freaks. When the dildo came out of Myra’s ass it left a gaping inviting hole so I kneeled behind her and easily slid my dick in past her sphincter, It was still incredibly tight, Myra whimpered a little but then quickly reassured me she wanted my cock in her ass. Casey moved in closer and said “im so proud of you baby you look soooo sexy getting fucked in your tight little ass”. Casey could see that I was getting close and leaned over and whispered into Myra’s ear: I’m taking this one baby”. I really started to dig it when she said “baby”. The way she said it was a real turn on. I went pretty easy on Myra, no hard banging but I was going in and out pretty fast, Myra kept looking at me over her shoulder while I was fucking her, fuck if her face wasn’t sexy as hell, the way she looked and the faces she made certainly made her look older than 10. When I was ready to come it was my turn, I grabbed Casey by the hair and shoved my cock as far in to her mouth as it could go, then I held it there until she gagged, I let up and she took it on her own to shove her mouth all the way down until she gagged again. Casey continued to gag herself on my cock, she had spit and saliva dripping from her mouth and all over face. This went on for 4 or 5 minutes, I had cum but I was still rock hard and getting into gagging her. The girls came over and we’re face to face with her as she gagged and gagged, I knew what was coming next. Casey took her mouth off of my cock and pulled both girls to her face where they all exchanged cum, spit and saliva until it all disappeared. We fell out on the floor and laid there while we recovered. The boys being boys must have got bored, they soon went to their room to play a video game and there I was, laying on the floor with 3 beautiful girls trying to think about what was next. We didn’t have to think long as Callie said it’s my turn next. I still had two more asses to plug tonight. Myra got up and took Callie by the hand and headed for the bedroom, “comon” she said to Casey and I. We followed her into the bedroom and into the bathroom where Myra ordered Callie to lay on the floor, Callie excitedly got on the floor, Myra squatted over her and filled her mouth with pee, Callie swallowed the first bit than held the rest in her mouth, she stood up and gave her mom a nice kiss with a mouth full of pee. Casey talking with her mouth full of Myra’s pee looked at me and said come here Dan, taste Myra’s pee. I couldn’t resist. These girls were just as sexy as any women could be. We stayed in the bathroom while the girls took turns peeing, each time sharing it amongst the three of us, then it was my turn, I laid on the floor, Casey squatted over me and smashed her pussy on my mouth and told me to eat her cunt, as I did she started to dribble and pee, I grabbed her by the waist and pulled her hard down on my face, she couldn’t control it anymore and let loose the rest of her sweet juices. The girls gathered around me on the floor and I did my part and shared it with all three of them. We went out to the bedroom where we slowly worked on making me hard again. I have never fucked so many times in one night as I have in the last two days. Callie took some initiative and started rubbing oil all over her ass and in her asshole even inserting her finger into her own ass. I joked with her, “are you going to need me” and with her cutest little girl pouty face said “yeah I want you to do me like you did Myra”. Casey was laying on the bed on her back rubbing her pussy, I moved Callie on to all fours over he mother. Immediately Casey started fingering Callie’s ass and kissing her crazily. I moved my dick into position and rubbed it all around Callie’s ass and slowly pushed it in, Callie’s asshole seemed like it was tighter than Myra’s. As I was pushing my cock slowly into Callie’s ass she slammed back hard and finished getting my cock all the way in. Casey and Callie were making out like a couple of wild animals underneath me. Now Callie was rocking back and forth as hard as I was shoving forward, Callie was truly loving my hard cock in her ass. When it was time I asked Casey, what was now my standard question: “where do you want it”? Casey, in her hottest sexiest voice yet said “I want it in her ass, I want to suck it out”! Hearing that made me explode my biggest load yet into Callie’s tight little ass. I backed up and Casey slid out from under Callie and said “stay there baby, mommy’s gonna clean you out” and then she got behind Callie and sucked every bit of cum out of her little girls ass. Callie turned over and laid on her back and Casey laid over top of her and kissed her for what seemed like forever, cum was smearing all over their faces. When they finished kissing they took turns licking each other’s face. Myra came to me and kissed me and once again we all fell out on the bed and it seemed as if Friday night was coming to an end. We laid there for a bit, the girls were talking about little girl stuff and Casey was laying face to face with me with half her body on me. At that moment she didn’t speak she just looked me in the eyes. She reached over and started stroking my cock again… after a couple minutes I was at attention and ready to go. Casey kissed me and said OK baby, you got one more tonight! She said “I want to sit on you backwards while you fuck my ass realllll slow. I want to watch my girls feast on my pussy while I sit on your cock”. I asked Myra if she would go get the oil and Casey blurted out “No, I don’t want it”. She sat on me and guided my cock into her wet pussy, this was all the lubrication she wanted, she rose up and sat back down on my cock, this time directing it into her pretty asshole. With her little 5’5” 105lb frame her ass wasn’t much bigger than her daughters. I heaved my hips and pushed in all the way, I have to admit I was surprised at how fucking tight her ass was. She swayed up and down on my cocky& as the girls got off of the bed and knelt down on the floor between her legs. Myra and Callie took turns giving their momma some fantastic pussy licking. I reached around and cupped Casey’s tits in my hand and began pinching and pulling her nipples, with one hand I grabbed her throat and choked her a bit, god that drove her wild and she said “I love that”. I was thinking about the 5 times we had sex before I came to her house, now that I know all the stuff she’s into I can see those 5 fucking encounters must have been kinda boring for her. Casey said “when you’re ready I want you to face fuck me as hard as you can”….then she smiled and said “don’t be nice”. We started getting a little rougher with my cock going in and out of her ass, she was now rising up and slamming back down on my cock , so much so that the girls were having a hard time keeping up with her. When I was close to coming I got up and grabbed Casey by her body and threw her down on the bed, I pulled her down to the end of the bed head first so that her head was hanging backwards off of the bed. I slammed my cock in to her throat and kept it there until she started to gag I face fucked her as hard as I could (without really hurting her). The girls got right next to her face on either side, they watched intently as my cock gagged their mom over and over again, when I was ready I pulled my cock out of her mouth and squirted a huge load all over her lips and face and I looked at Myra and Callie and said “there you little lovely’s, clean mommy up”. The girls did as they were told were very erotic as they licked and sucked the cum off of their mom’s face, %we all laid on the bed staring at each other, Casey was running her fingers thru Callie’s long blonde hair (actually bright white hair) and told her “I love you my little baby girl, you are so sexy”. We all laid there, everyone was looking tired so I asked them if they had had enough, Callie who I think could be a 11yr old nympho said “I’m not tired, I could do some more”. For the next hour or so Callie and I just laid there, kissing and touching, rubbing and an occasional finger. Casey had run out of gas and was just laying there staring at us and smiling, Myra had fallin asleep and things were really peaceful. Before we went to sleep Casey asked in a real quiet sexy voice, “are you going to stay thru Sunday”? After a minute of looking at Callie’s sweet little face I answered back, “if you want me to”. I no more got it out of my mouth and Callie blurted out “YES”. Casey said that her kids really liked me and was hoping that after this weekend maybe we could mix some normal things in and have some normal family fun. I have to admit the “family fun” made me a little nervous but after weighing the pros and cons I decided that I could show the kids some good times as long as they didn’t turn into rotten little brats. I fell asleep with a thousand thoughts running thru my head and Callie draped over me. it was a great night.
If You Like This Story, Stay Tuned For Day 3.
👄This will be the best oral sex you have ever experienced.👅