The hardest part of the school year and the winter was finding opportunities to explore my newfound feminine side. Often times I would sneak my bra and panties into the bathroom and masturbate while I replayed everything that happened in the back seat of Larry’s car in my mind. I would never forget touching his cock, feeling him get hard, the taste of his cum, and the satisfaction of knowing that I had the ability of making a man reach such sexual highs. I rarely took more than a few minutes for my own cock to be erupting with cum at the thought. But unfortunately, the “next time” for Jenni was nowhere in sight.
That night was also the last time Missy and I were able to connect for quite some time. After the kiss in the bathroom, Missy attached herself to Pete and was wasted to the point where Pete had to drive us home. The original plan was that I was going to spend the night at Missy’s house but with her passed out Pete and I both agreed that would be a bad idea. As I removed my makeup, I started to try and come up with a reason why there were curls to my naturally straight hair not knowing if I would be able to even get them out. I thought about how long I was going to have to conceal my killer bikini tan lines which were even more pronounced than I had believed. I let myself out and took the walk of shame to my own house.
I was up super early the next day, grabbed a shower, and was out the door before anyone was awake in my house. I walked over to Missy’s house but Pete’s car was still there. I just kept walking.
It was nearly a year before Missy and I connected again. There were casual hellos here and there but something had happened and I wasn’t sure what exactly I had done to earn this extremely frigid cold shoulder. It was early August and I knew Missy was packing and getting ready to head off to college. One day, before heading down to hang with the boys, I walked upstairs and found her.
“Hey, Mis. So you’re off to college. WOW,” I said making incredibly awkward and meaningless small talk. She looked at me with a funny, slightly disappointing look.
“Come in and close the door. Lock it.”
“OK. What’s going on?”
As I walked toward her, Missy got up off the ground, slid off her shorts, removed her top, and was standing completely naked in front of me.
“Would you fuck me? I’m talking right now. Get naked and fuck me.”
I stood in awkward silence.
“Or would you rather fuck my boyfriend Pete? Because I can call him and he can come over. I’ll get you all dolled up and he can fuck you right here. Or do you want to suck his cock?”
“Missy, what the fuck are you talking about? Why would I want to fuck your boyfriend or do anything with him?”
“Think back to last year, you know the great day I created for you. The ‘greatest day of your life?' Let me ask you when I was drunk and passed, was what I gave you not enough? The blowjob? Larry? I guess you figured you’d see if you could get a little more action. One cock just wasn’t enough that night?”
“No way. Stop right there. We got you up to bed and both decided I should leave. I fucking went downstairs, took my makeup off, changed, and left. I never even saw Pete again that night and certainly never wanted to fuck him.”
“If that’s true, then come over here and fuck me. I’m fucking serious.”
As conflicted as I was about my sexuality, I was one hundred percent certain I was going to fuck Missy right then and there. I could feel my cock getting hard as I walked toward Missy, taking off my shirt. Her hand reached between my legs and grabbed my cock as we locked onto each other’s eyes. She released her grip and pulled down my pants, the two of us standing naked in her room. We started to kiss, my hand starting to touch and explore the body I secretly longed for years. She took my hand and led me to her bed.
“My parents are gone to dinner and my brother doesn’t know you’re here right?”
“I came right upstairs to talk. No one knows.”
“Pete and I broke up months ago. He cheated on me that night after he brought me home, in my own house with some total whore that he met that night. When I confronted him he blamed you. He said you were overly flirtatious and at one point offered him sex. He said he couldn’t stop you because you were all over him.”
“That is not what happened at all.”
“I know. It took me a while to figure it all out. I was angry and very stubborn so even when I did finally find out the truth I was still so mad, I didn’t want to talk to anyone, even you. I’m sorry. I should have known better and not been such a bitch.”
“You seriously should have asked me. You have been awesome to me and I would never have done that to you.”
Missy took my hand and led me to her bed. We started kissing again. Her one hand started slowly stroking my cock while her other hand took mine and guided it to between her legs into her wet pussy. I slowly slid one and then a second finger in, starting to finger her slowly. Her body and the touch of her skin were heavenly. Her hand slowly stroked my cock before eventually telling me she wanted me inside her. I slid my fingers out as she guided my dick between her legs and to her lips. I slowly slid my now rock-hard shaft in, her pussy wrapping tightly around my cock. She moaned quietly in delight.
I could feel Missy’s pussy engulfing my cock, pulsating as I inserted deeper into her until I had filled her completely. I slowly withdrew, pulling my cock out until the tip was at her lips, and then slowly started to fill her up again. My mouth and tongue left hers and licked down her neck to her beautiful tits. I kissed her erect nipples softly and then starting sucking on them ever so gently. Everything about her was perfect. There were very few words exchanged over the next several minutes. My pace quickened and my thrusts into her became harder and harder. Her legs wrapped around me and I could feel her nails digging into my back. I felt sudden warmth overcome my cock as she started to cum. Moments later I felt my cock explode wave after wave of cum into her pussy, her hands now on my ass helping me push deeper into her.
“Don’t pull out. Stay inside me and fuck me again.”
After a moment to catch my breath, I started again, marveling at how hard my cock was and the pleasure I was bringing this once untouchable goddess.
“I want it hard in me. Fuck me harder,” she whispered.
I gladly did for the next fifteen minutes until I came again and the two of us collapsed onto each other, a complete hot and sex-drenched mess.
“I’m conflicted,” she said.
“Conflicted? As in if that was that was or wasn’t as great as I thought it was? I mean, I thought it was pretty good.”
“No, the sex was really great. I just don’t know if I like Jenni or Jeremy better than the other. You’re a super sweet guy but there is something about Jenni that I’m really drawn to. Either way, I do love your dick, even for a high school dude.”
“Well, Jenni has been out of action for a while for sure. It hasn’t been the same without you. Even just to say hello. I’m sure she would love to be with you just the same.”
“OK, be honest. How long have you wanted to fuck me?” Missy said as she climbed off the bed and started to get dressed.
“Are you being serious? As long as I knew that fucking was a thing. You have no idea how much all of your brother’s friends would have wanted to be where I was tonight. You are so fucking hot. Seriously, jealous.”
“They would want to be in my pussy?” she said with a laugh. “That’s sweet of you to say. But seriously, I have another question. What the fuck are you doing lying naked in my bed? Twice wasn’t enough? Get the fuck out of here.”
There was the Missy I knew. I got up off the bed and grabbed my shorts off the floor. As I was bent over Missy jumped in behind me, slapped my ass, and started dry humping me from behind.
“One day I’m going to fuck this ass so hard you’ll cum without me even touching your cock.”
“One day,” I said with a smile.
“Now get the fuck out of here before someone realizes I just fucked you.”
I left her room and quietly made my way down to the basement. The boys had no idea I was upstairs living out all of their wet dreams. The experience with Missy was everything I thought it would be. I would see Missy once again before she left for college and even then we could only sneak in a one-minute kiss. The gap between high school junior and college freshman was as about as big as I imagined. She found a sorority and a new boyfriend. We would see one another on breaks and even the following summer from time to time. Times were different.
That was until over a year later when I got the invitation from Missy for Jenni to join her at a Halloween party on campus. It was an invitation that Jenni could not refuse.
