Double the Fun

My dad remarried when I was 18. He had migrated from Florida to New Jersey after college. All his adult life, he had been a theoretical physicist working in the NYC financial district. When he met my mom, they married and got a place in the Connecticut ‘burbs. We lost my mom on 9/11. More recently, he rekindled an old flame from his high school days in south Florida. She was now divorced and lived close-ish by (also in Connecticut.) She worked in NYC too. They went on the sly for a while and then, when I was a junior in high school, they decided that they were getting married and that we, as a family, were all moving back to their hometown, (near Tampa) in Florida. Right before my senior year no less. In their opinions, the only time we could blend our families would be to rip us out by the roots and re-plant us in the fertile soil of southern Florida.

Dad and I had been on our own for 12 years and it was only normal for a widower to be attracted to another woman eventually. And I guess a woman his age might have a kid my age. But what is the chance that that woman would have two completely stunning daughters (both nearly my age). The girls were a complete surprise. It all was a surprise, but the girls were a total, complete and utter surprise.

It wasn’t like we got along immediately either. Mostly like three alpha dogs… growling, posturing, sniffing each other out. Then, it went really fast. I guess that was for us, not for them. They already had that high school “one that got away” history and then they kept this new thing low key and hidden until it was a real big thing and then it went really fast… for us.

News of their dating soon became news of their engagement and then we were the best man and their bridesmaids at their wedding. Then came news of our moving, and the inevitable “blending” of our families. It didn’t go too rough. We moved to near the beach and it never snows here. The girls are super-hot so my dick took a real beating at first. Both adults have long commutes into the business district so they must leave early in the morning. They say that leaving the “NYC crazy” was worth it.

My new sisters… Allie (20) is in college in Tampa at South Florida U and Claire (18) is in high school with me. They weren’t used to having a guy around in the mornings so they would walk around half dressed. Not truly “au naturale” (with bare asses-in-the-wind) but exposed enough to set my teen-aged mind on an in-the-gutter-walk-about. Nothing a firm hand couldn’t handle though. Early on, I went through so much Kleenex they must have thought I had long covid. That ended when my older sister (Allie) walked in on me in my bedroom, banging my fist.

She was nonplussed. Walked right up and called me an idiot. I was a bit set back. A beautiful college girl walks in with me lying there atop my bed with a left hand full of tissue and a well lotioned right hand full of dick. Busted with nothing I could use as a plausible defense. Fight, flight, or freeze. Couldn’t fight, dressed as I was there was nowhere to run, so I froze. She sat down on the edge of my bed beside me, then reached for some tissue and said, “Can I give you a hand?” With that, she then laid down, wiped the head off, and started stroking. Nonchalantly, she said, “I’ve never masturbated a guy before, so you’ll have to tell me what to do.” She was grasping the shaft too tightly, so I asked her to “adjust your grip and let it slide up and down like I am inside you.”

“Not so fast boy-o, I agreed to do this, not to do that.” I rather enjoyed the feel of her body on my bed, her breath on my neck, tits on my back, and her hand on my dick, so I felt reassurances might be in order. “You have nothing to fear from me, I’ll never take what isn’t freely offered,” I said. “Good,” she said, “then we have a workable arrangement.”

“Claire and I have been discussing you and we would like to work out a larger agreement. Teach us how that thing works and you won’t be whacking off. Leave us unsatisfied, or worse, leak that we had a deal and we will see to it that you’ll and ‘Mr. Stubs’ here never date again.” Then she put my dick in her warm, silky mouth and I forgot what I was going to say to her next.

She might not know how to give a hand job but she wasn’t bad with her tongue. I ask her to go a little faster, and she said, “not this time boy-o” and hopped off the bed, leaving me worse off than when we had started. She laughed and said, “I just came up to get your lazy ass downstairs for breakfast.”

Strange looks aside, breakfast started pleasant enough. The girls were having fresh fruit and yogurt with a sprinkle of granola (which seemed to be their go to). I was having typical boy food: heavy carbs coated in carbs floating in a bowl of milk. I had just filled my mouth when I nearly choked. Petite, angelic Claire clearly asked: “When are you going to show me that trophy cock that you are so proud of? Allie tells me that she even helped you polish it.”

I decided to not freeze this time. This time, I’d go on point. I got up and slowly walked up to her. “Coast is clear,” I asked? Allie answered “Would she have asked if it wasn’t.” I unzipped and pulled out my quickly stiffening dick. Ooooh, nice one… I guess… not too long and its not too fat… curves to the right, you’re right-handed– I see… then she slurped it. I mean she sucked it up into her mouth like it was a Jello shot. She bobbed her head a couple times to get it hard and then she… stopped? Then she said: “something to remember me by,” and kissed the tip. Shit, shit, shit. I was harder than Chinese Algebra.

No amount of visualizing “naked grandmas” doing deep knee bends was going to fix this. I quickly shot back upstairs and took a cold shower. Damn, any harder and I’d need an icicle up my ass to deflate it. For safety, I put on some speedos so I could keep my dick tucked down. I barely made the bus. In public Claire and I we were distant. You know, like proper siblings. It helped. I made it through classes even though my bent-back dick got painfully hard every time I thought too long about the events of this morning. School let out early so I went straight home after soccer practice and got home before dinner for a change.

Alice, my new mom, was attempting to help Claire with her “math” homework. My dad was late at the office again. Allie was upstairs somewhere and just as I was heading upstairs to drop off my gym bag, Alice asked about my homework. I replied, “I did it at 6th period study hall before practice, I am all good to go”. Then she asked me to have a look at Claire’s and I quickly dropped my bag off and went back down and sat down beside Claire. At a glance, I could see that she was well past my level. That was Particle Physics, not just math. I could help her study–as a human flashcard maybe– but I wasn’t going to be of any help explaining it. She would need to wait for my dad. Claire gave me a smile and said she wasn’t having any difficulty, just doing some extra work to stay on top.

Allie came down as dinner was almost ready. She had been messing with her new toothbrush she said. She said that she got one because Claire got one on the advice of a friend that liked hers a lot. From over by the stove, Alice added, “she brushes her teeth for five minutes every morning and massages her gums for a good fifteen minutes almost every night. Maybe I should get one.” The girls were about to explode stifling their giggles. “I am more for “hand operated” myself, but I can try it and if I don’t like it, I guess they could always use a spare.” And wham… Allie clipped the shit out of my shin under the table, kicking me a glancing blow with the side of her shoe.

After dishes were done, we headed over to the den to stream something. By then, dad was home and he and Alice went to their study. In the den, we “kids” were playing the TV at a “camouflage level” and having a private conversation. I got chastised for the double entendre– hinting using tooth brushes as vibrators was forbidden. Parents weren’t supposed to know why rechargeable, multispeed, “rumble mode” tooth brushes are preferred by teen girls for their dental hygiene.

The next topic was… me. Had I decided? And I told them that I had decided to never date again. That teasing to the point of blue balls and sending me to school with my dick shoved up between my ass cheeks was an insult that I wasn’t willing to bear. Allie added, “Get with the program boy-o and you won’t have that problem. Wean us off our tooth brushes and we will wean you off your hand lotion…” Put like that, we immediately came to terms.

Alice and dad came in just as we were done talking and saw us as a stereotypical family unit. We were watching a TV show, laughing, and making snide comments at the TV. Our parents couldn’t have been happier. They let us know that they were going to be gone sailing for a couple days and we were going to have some rules while they were gone: I could go stay with friends if I wanted to but I couldn’t have any friends over. The girls had to spend nights at home and could have girls (but no boys) over. Allie said that she would be going back to college soon and would prefer family time to partying. Claire and I responded that it was getting close to semester’s end so staying home sounded better. We could finish studies and then Allie said that she had a friend named “Betty” that she wanted to expose me to. Claire almost did a spit-take when Allie said that. (Something fishy going on there.)

The days went by slowly as we awaited our parents much anticipated sailing trip to the Keys. The girls kept their promise to stop torturing me as they continued their search for dental hygienic perfection. I was under strict orders to not “abuse myself.” Evenings were nice, Claire is impressive. A shy bookworm but she is so sweet… an emotional “bull in a china shop.” Underneath all that “smart young woman driven to excellence” she is a kind hearted, uptight babe that really, needs to get laid. When she decides to start dating, she is going to be a real heart stomper until she gets her head on straight.

On Wednesday, I thought I saw her at the fence near the stands during soccer practice. I didn’t take her for much of a sports fan but someone looking like her hung out in the stands, reading a book and watching practice. When I looked for her afterwards, she wasn’t around. I didn’t think much about it so I didn’t ask about it at home. Then on Thursday I saw them again and this time, I didn’t wait until after showers to find her. As we were clearing the field, she was leaving the stands. It was Claire. I stopped her and asked her to wait up for me so we could catch a bus ride home together.

She said that she was walking. I offered to walk with her either sweaty or clean but I had to grab my books either way. She waited while I showered and then we walked. She asked about soccer and why I played. I explained that playing was fun and I wasn’t good and many things but I was good at soccer. I liked defending and assisting. She said that most people felt excited about scoring. Then she mentioned that my contribution was central the team’s scores in our last 3 games. If I hadn’t made those steals, we wouldn’t have won. I hadn’t realized she had even been watching. I asked her about her interests and she cleverly dodged. She said that she was more of a “mathlete” and the school hadn’t fielded a girls’ soccer team in years. So, if she wasn’t interested in sports, I asked if it was a guy and she blushed. I pressed to find out who and she flat out refused and then she added: “no worries, he is just an idiot.” I answered that any idiot that had her attention was a lucky one indeed. Maybe he would wake up in time and not lose her interest. She answered, “Yes, maybe.”

She then changed the subject and said that I wasn’t given proper credit for my play. That she loved the way I’d come from deep behind, sprinting like my ass was on fire into an opposing team’s well-orchestrated play and just steal the ball. Then I’d reverse field, and take the ball back up field and do a chip shot to that guy that takes all the credit. I mentioned that he was an ace shot and no amount of bravado makes a shit worth of difference if there is no follow through. You are great at the lead-up and the face-off. You just need some work on your follow through and then you will score, I am sure of it. I think you just look at the ball too much. You don’t look at your feet at all until you have the ball and then you think that you can’t trust them.

That night, I asked Alice about Claire and soccer. Alice gushed on about how Claire used to love playing city-league but she aged out. Middle school fielded a team of 5-a-side but high school didn’t. Then she bragged about how Claire and I played a lot alike but that Claire “took the shot.” She didn’t always hit but she relied on her mates to cover for her misses, not to take her shot. Then she suddenly realized what she had said and apologized.

The next day, Claire was waiting as usual. This time she had some soccer kit on. She goaded me a bit and we started practicing a bit on a 5-a-side field in a public park. The goal and field are much smaller but you can still use it for practice a bit. Fun thing was, Claire took off her shirt. She wore a sexy sports bra… and I didn’t stare at my feet. We wound up getting others interested and made coed teams and had a blast. It was open and given how the game was played: us with no goalie and I was trying to seal the ball. If they could score, they got the point. I had to steal and to score against their goalie. Much fun. Maybe Claire isn’t such a hard ass after all. We left the park and walked home. She was the happiest I had ever seen her. She might be a “mathlete” but she really loves playing soccer.

Soon it was Friday and the car was packed. The parents would be on the road at first light. At dinner, the girls were at a Christmas Eve level of giddy. I was all jitters looking forward to the weekend as well. “Blow University” would be in full session from the time they left until 10 days later. I had saved up and the girls were going to teach me a bit about giving head too. The debauchery would start first thing Saturday morning. (And I was so looking forward to being “de-bauched.”)

I awoke to the girls hopping on my bed. Allie said, “I sure am glad you got a full-size bed. “All we got were singles.” Claire added, “Do you think that they knew we would all meet here”? Allie responded, “No, I think this was meant to be the guest room.” My dick was stiffening at the peep show of titties I was getting as the girls moved around. Allie sat up and then she kneeled, lifting her nightshirt bottom, and revealing that she had no panties on! “See,” she joked, “I brought Betty!!!” Then she sat back down. But first we must meet the “terrible night snake.”

In a serious tone, Allie instructed her sister, “Set it free Claire.” Claire looked at her like she wasn’t too sure what to do. “It might ‘spit’ at you but it can’t bite. Reach over and set it free.” Claire crawled forward and kneeled, then I kneeled. She reached over and pulled my shorts down, setting my dick free. My shorts were now around my knees so I was hobbled, I sat back and lightly kicked my legs free. Allie continued. “I’ve been having sex for over two years, almost three. Claire is still pretty much a virgin. You are a virgin too, right boy-o”? “Yes,” I answered bashfully. Allie interjected, “Hear that? If you jump him first, you can have a virgin Claire; or, I’ll jump him and you can have him right after he gets some experience.” Claire’s forehead wrinkled then she moved forward. “No, I want him– now.”

Claire and I switched positions. She laid down and I kneeled beside her sister. Allie was going to be the conductor of this orchestra. Allie asked, “Do you have any condoms”? I looked at her and sheepishly said… “no”? She responded… “you idiot”! And handed me one. “Don’t put it on yet. I think you have a hair trigger so let’s get that taken care of first.” Then she pointed to the spot on the bed beside Claire’s shoulder.

I “walked” on my knees over beside Claire, and with Allie’s coaching, Claire’s mouth soon had me so hard it was getting difficult for me to breathe. Then she asked Claire to take her hands off my cock and just use her mouth. When she made swallowing motions and rolled her tongue around, I knew I was done for… Claire didn’t dodge, she attacked. My ass cheeks were clenched so firmly, they were welding together. I leaned over and put a hand on a wall to steady myself. Claire pulled back and Allie told her to take her hand near the base and pinch it off. I came but none came out, it was pinched off. When I was done with my near orgasm, Allie had her lick a dribble of cum off the head. When she did, I lightly convulsed and almost cramped. There was a hint of a musky smell coming from Allie’s direction.

I went to put the condom on and Allie said, not yet, hand it here, boy-o. Get her warmed up first. Crawl down here between her knees and say “hi” to *her* Betty. I went down as I was asked and got face first with Claire’s pussy. It was soft and smooth with faint hairs just starting to announce her womanhood (not a neatly trimmed, well-travelled “landing strip” like Allie’s). As I inched close to her, I could sense a slight smell of Claire’s perfume mixed with a hint of her feminine musk. Her thighs were warm and her skin was extremely soft. Tan lines starkly marked her heretofore “forbidden zones.”

Allie touched her sister clinically and introduced me to her mons, vulva, labia minora and majora, vagina, and clitoris. Then she told me to kiss them and lick them to get used to how Claire responded when I did so. That sometimes what was “ooohh” last time could be “ickkk!!” this time; and, I’d have to crack the code. I did figure out that the clit was the destination; but that I shouldn’t go straight for it. That I should play with her tits and vulva first. Basically, tits first and then, after “Betty” started to open, play with the parts that were open to me. Then Claire mentioned a special spot behind the mons… behind the pubic bone even… she said it was called a “G-spot.”

I have long fingers and I felt for it with the pad of my finger but couldn’t feel a thing (not that Claire didn’t appreciate the diligence of my search). Then, after Claire’s pussy was fully “blossomed,” (as Allie calls it); and, her clit was erect and exposed. I could feel a rougher area near where Allie described that “spot” should be. By now, Claire was really aroused (and I was too). Allie looked over at me and said, “suit up boy-o.” and tossed the condom to me.

I fumbled as I put the condom on but I did get it done and I got between Claire’s legs and placed the head of my dick on her pussy lips and pressed slowly. As it sank in, I made short back and forth strokes as I pressed on. Claire said “That… That… That… feels good. I felt some resistance and Claire said ouch! As Claire “ouched,” Allie mentioned there was still some hymen in there that could hurt for a bit. She told me to push through, then hold for a second and let her catch her breath and then go again. Claire was obviously uncomfortable so I stopped for a bit. While we were resting, Allie told me to remember exactly where the G-Spot was because I should “aim for it” with my cock “when the time came.”

We had started back and Claire… no– *we* were enjoying it. Allie had us using our hips to rub and to grind. It was starting to be a bit more than I could handle. It appeared to be a bit more than Claire could handle too. She had pulled her knees up and I could see that she was maximizing friction on her clit. Then it hit me, If I pressed down and forward on her knees, it’d rock her forward just a little more, I might could rub the back of the head of my dick on that spot and while bottoming out, I’d be rubbing against her clit. I quickened the pace and it was feeling awesome, I could feel my scrotum contract, it was no longer touching her as we slowly, rhythmically, slapped together.

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the “A” icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I continued this trial of my theory and was met with a purring of approval from under me. The friction on her clit had lessened now though. Her finger tips quickly replaced it. Claire was squeezing her left tit and rubbing one out with her right hand’s finger tips while we screwed. Since I was relieved of clit duty, I again sped up the pace and renewed my task… this time, I pulled her knees back and sought to use her pelvic bone as a fulcrum to rub my dick on *that spot*. I held her ass rotated and steady with my hands on her knees and used my hips to assail “her spot.” If I wasn’t hitting it, I had to be close. My relentless pounding eventually stormed the palace.

Suddenly, her pussy was twitching. Then it spasmed. Then it convulsed. I am not going to lie, somewhere between the first twitches and the second spasm, I came. I didn’t slow down though… instead, I sped up. I kept coming… through the spasms and into the convulsions. Her pussy was trying to eject me and I was fighting to stay inside. Damn. That was so much better than I could have ever imagined. After her orgasm started, Claire put her arms around my neck and hugged me close to her. She was bent into a curl and was close to cramping when she went limp and was covered in our sweat and her disheveled hair.

Our hearts were beating fast as we lay there in post-orgasmic bliss, out of breath and entangled in each other’s limbs. Allie helped untangle while getting my now soft dick out and not spill any come in or on Claire. Boy-o, you really filled that rubber. Your cock has fresh sperm on it now, so don’t you dare get it anywhere near her Betty. You should go wash up. And bring a warm, wet, wash cloth for Claire. I cleaned up a little and fetched that moist warm wash cloth and a clean, dry hand towel for Claire.

When I returned, there was some drama going on. Claire was whimpering and Allie was attempting to soothe her. I did not know what to do. Did I do something wrong? What? I really like Claire and did not like seeing her like this. Was she OK? Could I help? Sensing that this was a private moment, I said “I am going to go down stairs to give you ladies some space here. I am not sure if I have a role in this but I really hope I do in the what-comes-next.”

Allie looked over and with a kind face, mouthed “kiss her, you idiot” and then aloud, she said “Hey, want to go start making breakfast?”

“Sure,” I replied. Then I said, “If it gets me in trouble, I’m in trouble, but I really want this… I’m not hiding it anymore.” I leaned over and kissed Claire on the top of her head. Then I whispered, “I seriously wish you weren’t my sister… by blood.” With that, she rolled her head over, looked up at me, grinned… and said– “You Idiot, I’m not!” I asked Allie, “Would you mind making the breakfast? I’d like to try some of that granola with you guys if you don’t mind,” and then after she left, I crawled right back into bed… into Claire’s arms and said, “Trust me, I know” and we kissed each other passionately on the lips.”

Leave a Comment