[MF] Fulfilling high school fantasies with an old crush. | 2016

Get comfy. This is a long one.

Edit 1: Changed her name from V to Vivian or Viv for easier reading. No more vendettas. Also, edited a minor typo.

So it's been a while since I've posted, but it's been a while since I've experienced anything worth posting. This story isn't going to be as kinky as some of my other ones, but it's been a wet dream of mine since high school, so I'd figure I'd share it anyway.

This starts back in junior year of high school when I met Vivian. She and I shared a class together--I don't even remember what class--and she slowly came into my friend group. I had a pretty big crush on her right away, but she fell for my best friend, and he and she dated for about a year, so I let my feelings go. By the time he and she broke up, I was dating another girl, so again, things never developed between Vivian and I. But that doesn't mean I didn't think about her.

Vivian was about 5'6" with hazel brown eyes and curly black hair. And by curly black hair I mean curly black hair. Like, basically-a-fro curly hair. She was a little on the thick side with perky tits and a big ass. We always teased her that Apple Bottom Jeans were meant for her.

But the best part about Vivian, and why I've always been attracted to her, was her personality. She's always been the crazy, I-don't-care-what-people-think kinda girl. And she's never been shy about her sexuality either. She's always been pretty open about talking about the guys she's been with or about what she's done sexually. And she's always been the type of girl that flirts a little too much at parties.

I remember the first time I was ever straight-up aroused by Viv was after school one day during our senior year. It was late winter and I had just finished wrestling practice and she had just come back from swimming practice. (They practiced at an indoor pool.) I was waiting outside with some friends and she got off the bus, wearing baggy sweats and a big hoodie. Her hair was still completely wet and it looked like she hadn't even bothered to dry off. Then all of a sudden, while we were talking, she takes off her hoodie. Even though she still had her swimsuit on, because it was so cold outside and because she was still wet, her one piece was clinging to her body like I wanted to. I could see everything. I could see how hard her nipples were, how shapely her breasts were, and all of the curves on her hips and stomach. I was instantly hard. She didn't even seem to notice, but just dried off with her towel then put a shirt and her hoodie back on. That night the only thing I could think about was how tight that swimsuit was.

The two other times when we went a little further than strictly platonic friends should have happened during and after college. One night during my sophomore year she came down to stay with me in my dorm for the night because she wanted to see what my college nightlife was like. We were both single at the time and of course I was hoping that things might progress further between us, but I wasn't sure if she felt the same way. I asked her what she wanted to do and she said, "Well, why don't we just drink and see where the night takes us?"

Yes. All the way yes.

So before she came down I cleaned my dorm room better than it had ever been cleaned before. It was a single occupancy room, so I had my own bathroom and everything. I even snuck in a bottle of vodka into my room. When she came down we said hi and I showed her around everywhere and took her out to dinner at one of my favorite restaurants. The whole evening we were laughing and kinda flirting. I was nervous and turned on the whole night.

After dinner we came back to my place and started drinking. We had a couple glasses of vodka and orange juice, and were just catching up while listening to music. Then a song came on the radio and she perked up. It was one of the big rap songs that was popular our senior year. (I think it was "Cyclone", maybe? Some kind of banger like that.)

"Oh! Remember this one!" She jumped up and pulled me off the couch. She held onto my hand and raised her arms above her head and started rolling her hips. We started dancing together.

"Oh my god! Remember at prom when those two girls were grinding on those guys, and then they leaned over while holding hands and their boobs fell out?!"

"Oh man, yeah I do remember that! That was a crazy night."

"Yeah it was." She paused. "I fucked M--- in the parking lot that night."

"What?? No way."

"Yeah, in the back seat." She smirked. "It was hot." She turned around and started grinding on me. "So what did you do that night?"

I paused.

"I fucked K--- in my dad's truck behind some Chinese place."

"No you fucking didn't!" She turned around and slapped me on the chest. "You dirty little slut!" We both laughed and she gave me another one of those smirks. "Let's take a shot."

I poured us a round and we raised our glasses. "To old times," I said.

"To old times. ...and the new."

We tossed back our shots.

"Alright," I said. "Want to go downtown now?" She let out a whoop and headed out the door.

While we were downtown we drank way more than we should have. And she was getting very drunk. So drunk that while we were sitting at a booth, she was telling me all about the new tattoos that she got. Although, she was very loud and was also telling the whole bar about the new tattoos that she got. The whole bar who was now really interested in our conversation. Telling us about the tattoos that were on her lower stomach, right below her panty line.

"Look?" She said, as she unzipped her pants. "Aren't they awesome??" I jumped up and stopped her from pulling her pants down completely. A lot of guys shot me dirty looks.

"Alright, Viv, I think it's time we maybe head home..."

"More shots!"

"Okay, one more when we get home!"

I helped her up and we made our way back to my dorm. When I got there she took another shot and turned around to me with a big, goofy smile on her face.

"This was fun."

"Yeah, it was. Are you feeling okay?"

"I'm drunk."

"I know. Why don't you lie down? I'll get some water."

She kinda pouted, but did as she was told. I helped her get in bed and turned the lights out, a little disappointed that the night had taken a different turn than I'd hoped. ...but then about thirty minutes later I spent the rest of the night making sure that she hit the toilet when she threw up.

The last time that things almost progressed further was a little after that when we had both graduated. This time I was single, but she was with a guy that she was dating. I had come over to see her since it had been a while. We had gone out for dinner and had some drinks while we caught up, and it was like no time had passed at all. And she was still flirty as ever. And I was still into her as ever. When we finished up with dinner, we grabbed a cab back to her place.

When we got into her apartment, she turned on some music and grabbed a bottle of Fireball from the cabinet and two shot glasses. "Ever had this before?"

"Yes. And I can't say I'm too fond of it."

She smiled. "Stop being a baby and do a shot with me."

"Yes ma'am."

We threw back the shots and I chocked a little. I hate that stuff. She laughed through chokes of her own. "Alright, I'm going to change into something more comfortable. Don't get too far ahead of me now."

I poured a glass of water and made my way over to the radio. As I was flipping through the stations she came back in. She had changed into a loose t-shirt and some yoga pants. The shirt hung loose over her breasts and her yoga pants stretched around her ass to the point where I could see the small thong she was wearing underneath them.

"Well," I said. "I didn't know we were getting so dressed up." She play hit my chest.

"Shut up and take another shot."

So we continued to flirt and drink to the point where we were both blurring the lines of what was okay.

We started dancing and she was rubbing her ass all over me. There was no way that she didn't feel how hard I was. I slowly moved my hands down her arms and across her stomach. I rested my chin on her shoulder. She turned her head towards mine. I could feel her breathing get heavier. I took her hands and made to spin her around, but she wasn't expecting it and she completely lost her balance, making us both fall over. I was able to kind of catch myself at the end, and fell on top of her. I sat up on my knees and she rolled over onto her back, putting both of her legs around me. I leaned forward, over her. We looked into each other's eyes. She put her hands on my chest.

"You know, I don't think I ever really apologized for throwing up all over your bathroom when I came down that one time."

"Yeah," I chuckled. "That was rude of you."

We stayed like that for a minute. I can't tell you how badly I wanted to kiss her. But I couldn't. I leaned back. "I think it's getting pretty late."

"Yeah. It is."

"This was fun though."

"Yeah, it was."

I stood up and helped her to her feet. "I'm going to get ready for bed," I said.

"Okay, I'll go get you some blankets from the other room."

"Thanks you."

She smiled as she walked away.

A few minutes later she brought me the blankets and told me goodnight. Before she left though, she stopped in the doorway. "Hey. Thank you. For tonight." She looked sad and happy at the same time.

"Yeah, of course. I had a lot of fun, Viv."

She gave me a smile and closed the door. All that night I thought about how I wished our timing was just a little bit better. After that night she and I kinda lost touch. Nothing bad or anything, just life getting busy for each of us.

That brings us to the present. This year is our ten year reunion for high school. I can't believe that I'm so old now. We started getting Facebook notifications earlier this year about the reunion. If there's one thing that I learned from it, it's that I can't believe how many people went to my school that I either don't know or don't care about. But the weird thing is that most of my friends either weren't responding or weren't going at all. I guess that makes sense, as most of us have moved out of state. And most of my other friends all have families now. But my parents still have the house where I grew up, and they were going to be at their house out of state, so I decided why the hell not? I thought it would be fun to visit the old stomping grounds and maybe catch up with at least one or two people there.

Then Viv liked my post about going.

So I messaged her, asking if she was going to go too. She said that she was. From there we started chatting just a little bit more, and a little bit more, and a little bit more, until it got to the point where we were texting every day. And snapping each other every day. I couldn't help but notice that she liked to Snapchat at the gym in her sports bra and tight workout pants. So I figured a couple snaps of me lifting weights wouldn't hurt either. And all of a sudden I was back in high school, crushing on this girl all over again.

I got into town the night before the reunion. It was weird staying in my old bedroom. It felt so much smaller than I remembered. Almost everything was the same, though most of my stuff had moved out with me. I didn't sleep well that night. Anxious and nervous and a little excited for what might happen the next night.

Viv got into town a couple of hours before the reunion. She was staying at a hotel fairly close by, so she asked if I could give her a ride. The reunion was at a local state park where we would all cook out and catch up over lawn games and beers. I said sure and headed her way.

When she came out of the lobby I had to keep from staring. She was stunning. Her hair was curly and frizzy like always. She had on big, dark sunglasses that completely covered her eyes. And she was wearing the sexiest dress I'd ever seen her in. It wasn't actually sexy or super revealing or anything like that, it was just how she looked in it. It was a simple navy blue cotton dress. It didn't have any sleeves and the top came all the way up to her neckline, and the bottom came all the way to her feet. But the way it hugged her hips and shaped around her breasts and stomach was just mesmerizing. She got in my car and leaned over for a hug.

"Oh my god! It's so good to see you!"

"You too! You look... stunning!"

She beamed. "Thanks. I opted for comfy, yet classy."

"Well, you look great. You ready to head over?"

"Yeah! Let's go!"

On the way over we chatted about the normal things. How work was going, how our parents were, yadda yadda yadda. When we got to the park, it wasn't as fun as I had expected. The vast majority of people there I didn't know, and the people I did know I wasn't exactly close with in school. Past the hey how are ya's, there wasn't really much to talk about. Viv and I kinda just stayed to the side and watched some people play horseshoes and corn hole. A couple of people brought Frisbees, but only one person was any good, so they quit pretty quickly.

I have to say though, while the people weren't all that great, the scenery was fantastic. It's a pretty wooded park, but the was the sun sets through the trees was stunning. As things started wrapping up I packed up my cooler and bag. I saw Viv leaning over the railing, watching the evening fade away. She was leaning with her arms folded over the rail, her weight shifted to one leg. Her dress hugged her waist and hips perfectly, and the dress rolled off to her feet. She looked great. I walked over beside her and placed a hand on her lower back.

"Oh," she said. "Hey."

"You okay? You looked like you were lost in thought."

"Hmm? Oh, yeah," she said. She stood up and stretched out her back. "Just thinking about old times, ya know? It's a pretty nostalgic day."

"Yeah, it is." We both looked out at the sunset. It was almost dark now.

"Hey," I said. "It's not late yet, and I don't really want to go home to an empty house. Want to go around the old stomping grounds?"

"Oh my god yes! We've got to see the old school!"

"Great! Come on, let's go."

We hopped in my car and headed over to the high school. It was like my room: the same, but completely different. It looked like it had had a few fresh coats of paint since we'd left, and the parking lot had been expanded, but other than that, not much had changed. There were a few new trailers, but that was it.

We made our way to the football field and I parked the car.

"You know," she said. "One time I skipped class and came out here and got fingered by D--- in his back seat."

"What?? Viv. Oh my god." I started laughing. "You're crazy."

"What? You're telling me you never fooled around out here?"

"No. Well. I mean..."

She play hit me. "Shut up! Tell me!"

"I was with K--- at the time. We came out here after she got off work one night. We went down to the field and started fooling around."

"I don't believe you. I always thought you were Mr. Goody-Goody."

"What? Me?" I blushed a little. "No, I wouldn't say that I'm goody-goody."

"I don't believe you." She opened the door and got out. "You're going to show me where it happened."

I followed her down to the field and led her over to the 25 yard line.

"It was right here. We were laying on the field and looking at the moon. It was gorgeous full moon. She was in my arms and we started kissing. Then... well, yeah."

"No, no, no. I want details."

"What??"

"Oh come on, I tell you all my stories. You can at least tell me one."

"Okay, okay..." I could feel my stomach turning a little as I started to get flustered. I told Viv about how kinky K--- was and how she liked to do it in public. I told her how we started by making out on the field, then how I lifted up her shirt and started to play with her breasts, and how she started to dry hump me, and how I was rock hard as she rubbed across my dick.

"Oh my god, stop!" She was laughing now. Her mouth open. "You are such a tease! That's all you did?"

"Oh, no. I fucked her over by the equipment shed."

"WHAT." This time she punched me in my chest. "NO."

I started laughing. "Yeah, right over there."

"Shut up. Show me." She grabbed my hand and dragged me over to the shed.

"Well," I said. "We were still on the side facing the field, so if you were down here you could still see us, but we were shielded from the parking lot."

"And what, you fucked her here?" She gestured towards the gravel on the ground. "That must have fucking sucked."

"No, no. She had her hands against the wall and I fucked her from behind."

"Oh..." Viv looked at the wall and looked at me. Then she blushed and looked away. "That sounds... hot." She looked at me with those big, hazel eyes. I walked over to her and held out my hand. She put her hand in mine. I turned her so her hands were against the wall.

"We were like this." I slid my hands down on her waist. I could feel her panty line through her skin tight dress. I rested my head on her shoulder and whispered in her ear. "I fucked her just like this. It was fucking hot." I pulled away from Viv. "Actually, it was fucking cold as balls."

Viv looked a little dazed then composed herself. "Um... w-what?"

"It was sometime during the winter. I remember because she was under all kinds of clothes and my balls were freezing in the cold. I remember that it felt amazing though, with the cold wind on my balls and how tight and warm she was."

"Oh my god!" Viv's jaw dropped. "You dirty perv!"

"We didn't have condom either, so I finished somewhere on the ground over here."

Viv full on double punched me in the chest. "You filthy whore! I thought you were a goody-goody! I can't believe you!"

I smiled. "It's true. I told you I wasn't so innocent."

Viv was quiet for a moment. She walked closer to me. "So. Mr. Goody-Goody." She leaned into me with her arms on her chest. I put my hands around her waist again. "Why did you stop that one time?"

I was a little taken aback. "Well, Viv, you were pretty drunk..."

"No!" She hit me. "The other time."

"Oh... Well, you had a boyfriend. I didn't think it was right."

"We weren't exclusive yet. We were still... testing the waters out."

"You never told me that."

"I know."

"You should have."

"I should have." She bit her lip. "You know, that night I waited up for you. I put on a sexy set of undies on for you."

"I didn't know that." We looked at each other for another moment. "I really wanted to come to your room, you know."

"You should have."

"I should have."

I held her for a second. She closed her eyes. I leaned in and kissed her. Her lips were amazing. They were soft and sweet and perfect. She opened her eyes and smiled. "I've been waiting a long time for that."

"Me too, Viv."

We kissed again. She put her hands around my neck and I slid mine around her waist. She started rubbing my chest, then slid her hands up my shirt and across my stomach. I slid my hands up her stomach and underneath her breasts. I let my thumb rub across them, slowly, until I could feel her nipples through her bra. She pushed me away and then pushed me against the shed. She came back to me and we started making out like teenagers.

We were all but fucking through our clothes when she bit my lip. She looked at me with come-fuck-me-eyes. "Fuck me. Right here."

"What??"

She turned around and put her hands against the wall. "Like you did before."

"Viv... I... We're still out in the open!"

"Shut up and come on!"

I looked around and didn't see anyone. I was all kinds of nervous. I walked up behind her though and started kissing her neck. She pressed her ass against me and started slowly moving her hips side to side and up and down. I started lifting up her dress and could slowly feel the soft skin of her thighs.

"Viv... God, you are so fucking sexy."

"Shut up and fuck me already..."

I started to unzip my pants. All of a suddern, the field was flooded with light out of nowhere.

"Fuck!" We both frantically put ourselves back together as we heard the car doors shut and the headlights cut off. The voices from the car started making their way down to the field.

Viv looked angry. "Oh fuck off, fucking high schools fuckwits."

I couldn't help but to laugh. "Oh hush, Viv. It is the summer. And it's a great night to get into some trouble." She smiled. We discretely made our way back up to the car.

"So," I said. "Where to now. Do you need to head back to the hotel?"

"I don't want to," she said, placing her hand on my lap. "Anywhere else you want to go?"

"You know, I'm staying over at my parents house. When was the last time you've been over there?"

"Oh my god! It's been forever!" She sat up a little straighter. "Are they still up, or..."

"Oh no, they're not home."

"Oh... I see. Well, I mean, I'd love to go see the place. You know. To see how it's changed."

I smiled. "Sounds good to me."

As I drove off, I slid my hand onto her lap. She held it with both of her hands. Then she slowly moved it down to her thighs, and led my hand right between her legs.

"Yeah?" I asked.

"Yeah."

She spread her legs a little and I started rubbing her through her dress.

"Oh, man, Vivian."

"Yeah. Me too."

"Jesus... If only I'd known sooner..."

"Just shut up and get us there quickly."

I started to speed as I slowly caressed her through her dress. She moved her hips against my hand and started breathing heavy. She grabbed my arms and started squeezing me tightly. I flexed a little. She liked that. She started moaning. I had to try and shift myself in my pants because I was rock solid at this point.

When we pulled into the driveway she threw the door open before I put the car in park and was waiting by the door. I fumbled for the right key in the dark and as soon as the door was open, she pushed me inside, closed the door, and threw me against it. We started making out and she ripped my shirt off. As she was fumbling with my pants, I lifted up her dress over her head and threw it to the side.

She was wearing a black bra and a small, black thong. Her body looked amazing. She ripped off my pants and stared as I flew full mast. She slowly grabbed it and started stroking it. I moved to take her panties off. We started kissing while she stroked my cock. I slid my hands up her thighs, and slowly across her pussy. She was soaking wet.

After a few minutes, I pulled her close, picked her up, walked back to my room, and threw her on my old bed. I got on my knees and threw her legs on my shoulders. She looked fantastic down there. I don't know how else to describe it, other than exactly how I'd hoped. She was freshly shaven, save a small patch above. I went down on her, slowly sliding my tongue inside her, then licking all the way up to her clit. I started flicking her clit with my tongue, then I started to suck her clit, then lick, then suck. With one hand I pushed down on her pelvic area since she was moving around a lot. With my other hand I slowly slid a finger inside her. Then another. Then another. Her hands made their way through my hair, pulling whenever I hit a good spot.

I slowed down, then started kissing her thighs and down her legs. I leaned back. She was breathing heavy. I climbed on top of her, letting myself drag across her body, teasing her as it pressed against her. I scooped her up, then rolled over so that she was on top of me. I unhooked her bra and tossed it to the side. She leaned back on her knees, on top of me. Her breasts were perfect in my hands. They were just too big to fit in my hands, but were still perky. Her nipples were amazing too, because they were slightly big, and a little long. They felt great as I twisted them between my fingers.

She took my hands off her and leaned down over me. With one hand she reached down between us and started to stroke again. "You ready?"

"Yeah. Grab a condom out of my drawer though."

She looked at me funny as she reached over and pulled a couple out. "Umm, before we begin, how long have these been here?"

I laughed. "Don't worry, I brought these with me. These aren't from high school."

She smiled and pushed me back on the bed. She slowly rolled the condom onto me. I could tell she liked the way I felt in my hand. She climbed on top of me, and slowly put me inside her as she started to ride me. She went slow at first. I could feel how tight she was. But soon she started to go faster and faster. Every part of her felt so amazing. From her tight lips which gripped me as she slid up and down, to her hard nipples which brushed against my chest with every movement, to her soft lips on mine.

I could feel myself getting closer, so I slid her off me and laid her on her back. I slid inside her, slowly at first. I could see her face tighten in pain, then pleasure. She started moaning pretty loudly as I went deeper and deeper in her. I moved one of her legs on my chest, and wrapped my arm around it and started rubbing her clit. I fucked her harder. She started to twist her nipples. So with my other hand I twisted her other nipples. I started fucking her even harder. I could feel her body tense around me. Her legs fought to straighten out. She looked me straight in the eyes. She slid me hand from her breasts to her throat. I slowed down. I was hesitant.

"Don't stop." She squeezed my hand. "Start lightly. I'll tap if it gets too hard."

So I started fucking her harder, and slowly started to choke her. I could feel her whole body move and tighten around me. I was so fucking hard. I was so close to coming. So was she. When I could feel her body start to shake, I closed my hand around her throat a little tighter and started fucking her as hard as I could. I could feel her cumming. I felt her body relax a little, but she was still moaning really loudly. I let go of her neck. I was so turned on. I was right on the edge of cumming, when she asked me if I was close. I nodded and got off of her. She ripped the condom off and started sucking me. Her lips felt amazing on my dick. She used them to push my foreskin back, and with her tongue licked me at the same time. I started moaning. She looked up at me and I nodded my head. She started sucking harder and faster. I exploded in her mouth. With every burst, she took me further in her mouth. Her spit and my cum was all over her face. She took me out of her mouth and smiled. She took a finger and wiped some of it up, then licking it off.

She ran off to the bathroom and cleaned up while I caught my breath. She came back a few minutes later, her tits bouncing with every step. Despite having just cum, I could feel a tugging from down below. She kissed me.

"So, want to watch TV or something?"

"Yeah, I could go for that. I'm hungry too. Want to order something?"

She smiled and put her hand on my chin. Then slid it down my body and grabbed my dick. "Yeah. Hurry up and meet me in the living room." I watched her gorgeous ass sway as she walked out of the room.

I fell back into my bed with the stupidest grin on my face, so many of my high school fantasies having come true.