I Dated The Wrong Sister Part 2 (F23M21)
Skylar really put things into low gear; after our first night, she would not do anything alone with me for over a month. I swear she introduced me to everyone of her 30 girlfriends. I learned all kinds of things about her; loves all kinds of music, she hates to cook, loves to eat, rarely drinks alcohol, never does drugs, loves rom-coms, is a huge hockey fan, and will fight you at the drop of a hat if you make fun of her height. Seems Sky is a judo black belt as are many of her friends, and I spent a painful Saturday morning being thrown around by all of them for three hours. I know nothing about judo, but I do know how to be thrown around by women who weigh about half of what I do.
I even had to spend four dates at her parents’ house where her mom apologized six times for Aria’s behavior, her dad dive times, and Jimmy told me ten times he warned me. Aria was never present. After three months, I just figured that Sky was too terrified of my size to want to do anything else but be friends. Hockey season was over, it was summer so Sky had nothing better to do than take me swimming at a local beach. See, I figured, that since she was so small, Sky would wear a bikini like Aria always did. No way; turns out all she had were one-piece suits; she explained she had a couple of accidents where she posted out and never wanted that to happen again.
We’re at the beach with twenty of her girlfriends, and every single one of them are wearing bikinis. They all are pretty flat, c-cups at the most, and I’m pretty stunned, when Sky pulled off her hoody to reveal the sleekest, sexiest, pink one piece I’ve ever seen. Don’t get me wrong, it totally covers everything, but it flatters every curve while still letting her nipples poke through. Sky let me apply sunscreen to her back and she returned the favor. We probably stayed half the day before she called it quits. She fell asleep so deeply, I had to carry her into her parents’ house. Her mom kind of giggled at that.
“Thanks for being a good friend Bobby; I’m sure Skylar appreciates that.” You have a nice day. It’s so nice to know you treat Sky with respect.” Yeah if I didn’t I’d have a broken arm or two.
I had time to clean all the sunscreen off of me, eat lunch and do dishes, before Sky came right into the house; the front door was open; “So, you just dump me at my house? What’s wrong am I not pretty enough to date?” Sky’s face was bright pink, her nipples were poking straight out of her bathing suit, and she was breathing kind of heavy. “Mom says we’re friends, just friends; that’s it?” I made the mistake of putting my hand out, but Sky took that as a threat, so in a second, she had my arm twisted around, I was on my knees, and Sky was growling, “All day long I see that big cock of yours bouncing around at the beach and we’re just friends? I don’t think so pal; you may break me in half, but that cock is mine.” Sky dropped my arm and started kissing me so fiercely, I was having problems breathing. “Get it out now! I want to see it.”
I stood and dropped my shorts and my cock was flaccid. Sky didn’t even need to bend down too far before she took me in her mouth and swallowed me whole. “That feels so good; you have no idea how much I wanted you to do this.” Sky was so good at getting me hard and pleasing me. She was bobbing her head up and down on me faster and faster. I was fully hard, but she had only taken about half of me down her throat since I was hard. “Here, let me return the favor.” I pulled off her hoody and shorts, before Sky took off her suit; her pretty pink nipples were so hard, I couldn’t resist. I was sucking them, licking them, and rubbing them with my thumbs. Sky was moaning in pleasure, so I slipped a hand between her legs and inserted two fingers; she was oozing a thick clear goo and she was ready to cum. As my thumb rubbed her clit, my fingers found her g-spot and just rubbed her raw until she squealed and came all over me. “I really need to taste you.” I put her in a chair spreading her legs wide. Oh she was sweet; I lapped at her juices as her legs shook with pleasure. I raised my head up to ask, “You like this? This is what you wanted, right?” Sky’s only response was to push my head down and hold it in place on her pussy.
“Oh Bobby, just like that, keep licking just like that, yes, you are so good at that.” Sky’s thighs shook with pleasure as her toes pointed straight out. “Oh baby, you know how to please me, you keep that up and I’m gonna, yes, yes, yes, don’t you even think of stopping.” Even as her thighs shook uncontrollably, Sky locked her feet behind my head and held me in place as she squirted all over me.
I’ve never had a woman come that much on me ever. We were both panting heavily, before I gasped out, “What else do you want?”
Sky grabbed my by the hand and dragged me to the bedroom. She pushed me on the bed to suck my cock; “You taste so good; you need to be nice and sloppy so I can fit you inside me. You’re just so big. But I need to try, I need you inside me.” Sky stood so she could straddle me; she lined my hard-on up with her pussy before she slowly lowered herself on me. “Oh baby, do you feel that? It feels so good, it’s like that cock is meant for my pussy; it fills me up som completely, it feels just perfect.” Sky’s legs shook as she bounced up and down on me slowly a look of pure joy on her face. In just a few minutes another orgasm shook her before she grunted, “From behind, I want to feel you take me from behind baby.” I went slowly and gently thinking I was too big; “It’s okay baby, you can give it to me; you feel so good, let me have it, let me have it all.” I wasn’t too rough, but Sky was enjoying herself; “That’s it baby, oh yes, like that, don’t stop, more, yes, like that, oh, oh, oh!” She came again harder this time her entire body shaking with delight as more of her thick goo oozed out of her. “I want to see! I want to watch that big beautiful cock wreck my pussy. Turn me over.” As soon as I did Sky gasped, “You didn’t cum yet? You’re going to leave me too sore to move for a week. I’ve dreamed of this, but, don’t stop; drive that cock into me.”
I watched my cock slide in and out of her soaking pussy, a smile on Sky’s face; “I dreamt about something like this, but I never dreamed it would feel this fantastic.” Sky used her pussy muscles to grip my cock as I slid in and out. “That’s even better; look at yourself Sky, you’re so beautiful, that’s it baby, push back against me. Grab me make me feel every inch of you.” Sky did not need any encouraging she made sure her pussy grabbed me with all her might and my cock was twitching like mad. I was worried I was going to cum and cum soon.
Sky laughed; “Little too late to think about that now Bobby; you’re going to flood me; give me that cream pie I’ve been needing all day.” I was getting a little out of hand; Sky was kind of squealing but she was bucking against me hard. “That’s it baby, deep and hard; make sure I feel those ropes of cum in the back of my throat; come on, give it to me.” We both came violently at once; both bodies shaking as we tried holding onto each other. It seemed like it took forever for us to stop shaking, but when we did, we were both happy. Sky led me by the hand to the shower; “Thanks Bobby; that was amazing. I guess I can tell mom we’re going to be more than just friends. You okay with that?” Sky had a firm grip on my semi-hard cock.
I shook my head no; “I am not okay with that, I am far too happy to explain how wonderful that is. Let’s get cleaned up before we get something to eat.”
Sky laughed as she reached for the body wash. “That sounds good; but I know what I’m having for dessert baby and so do you.” TO BE CONTINUED . . .
Posted Feb 15, 2026, 8:45 PM UTC