[FM] Playing Matchmaker Has Its Benefits

My first time wasn’t great. It wasn’t terrible or anything…it was just okay. I can’t say I really blame my boyfriend at the time. We were both young high school kids and had no idea what we were doing. But the bottom line is that it put me off of the idea of penetrative sex for a while. He and I would fool around, but we only had sex one more time and that wasn’t much better.

So when I went off to college I wasn’t exactly on the prowl for guys. I met plenty of new people and had a lot of new experiences, just not sexual ones. I lived with one other girl my first semester, Michelle. We didn’t meet until move in day, but we became really close friends over the first few weeks of school. Neither of us knew anyone else at school, since we were both out-of-towners.

A week before the end of our first semester, a guy Michelle had a crush on invited her to a pool party at his house to celebrate the end of the semester. Michelle convinced me to come along.

We spent the day getting ready, which mostly consisted of Michelle trying on all of her different bikinis and party outfits and telling her which one I thought would best catch the eye of her crush, Thomas. She eventually settled on a skimpy one piece that showed off her body really nicely. I could tell she was super apprehensive about seeing him at the party though.

“Just play it cool and tell him you like him,” I offered.

Of course, I had never asked anyone out so I wasn’t exactly the right person to be giving out advice. I thought I was confident enough to do it if the moment came, though.

“Easier said than done…you know how nervous I get around guys,” she said.

I just wore the only bathing suit I had, so there wasn’t much of a fashion show. I’m not gonna lie though, I looked good in it. It was just a traditional two piece, but it showed off my body. It’s deep blue color kept me from looking too pale. I didn’t bother doing anything with my frizzy auburn hair since I figured it was pointless since I was going to a pool party. Normally I’m a C cup and this bikini made me look even bigger.

We both threw on cute sundresses over our bathing suits and headed out. By the time we got to the party, the house was packed. There must have been at least 50 people there.

As soon as we walked inside and Michelle scanned the room for Thomas. He was standing across the room, talking with another guy. Michelle made a beeline right for Thomas, dragging me by the hand behind her. I’d met Thomas a few times and he seemed like a nice enough guy. I could tell he was into her because his face lit up when he saw her.

He said hello and nodded to the person next to him, “This is Chris.”

“Nice to meet you…” Chris trailed off, waiting for us to introduce ourselves. He flashed a smile.

“I’m Megan and this is Michelle,” I stammered, briefly losing my train of thought as I looked up at him and saw his smile. He was a good foot taller than me.

“I was just going to get a drink. You guys want anything?” he asked, looking at each of us in turn.

All three of us nodded.

“Four beers it is then,” he said and walked away toward the kitchen.

“So who is that? I’ve never seen him around before,” Michelle said.

“That’s Chris. I’ve known him since we were in kindergarten. He just moved here. He’s not starting until next semester but he’s crashing here until then,” Thomas explained.

There was an awkward pause between the three of us. I definitely felt like a third wheel.

I watched for a few more minutes as Michelle tried her best to make flirty small talk with Thomas as I stood next to them. I wanted to slowly back away but I could tell she didn’t want me to leave her alone with him.

Thankfully, Chris returned with drinks and spared me further third wheel awkwardness. He handed out the drinks and offered to show me the pool.

I looked up at his smile again and lost my train of thought. I shook my head slightly and said, “Sure. That would be great.”

We walked away, leaving Thomas and Michelle to talk alone.

Once we were outside, Thomas motioned to the pool and said, “Mission accomplished!”

There were people sitting around the edge, a few bobbing up and down in the pool, some swimming around and one couple making out while they floated in the deep end.

“It sure is a pool,” I said sarcastically.

“That too,” Chris said. “I meant I finally got you away from Thomas and Michelle so he can talk to her.”

“Please tell me he likes her! That’ll make things easier,” I said.

“Yeah right, Thomas is scared out of his mind to ask her out.”

“Michelle is the same way.”

We both laughed. My laugh turned into a snort and I could feel my face turning beet red. He flashed that smile again at me.

“I’ve got an idea…take out your phone.”

I pulled it out and looked at him.

“Send Michelle a message saying you know for a fact that Thomas likes her,” he said.

I typed out the message and sent it. Chris pulled out his phone and did the same. We both looked through the glass doors at Thomas and Michelle. They both pulled out their phones at the same time, feeling them buzz.

Chris looked back to me and held out his hand for a high five. I slapped his hand with mine and said, “We should start a matchmaking business.”

He laughed and said, “Should we go over there and make it super awkward for them again?” he asked with a mischievous smile. His smile was enough for me to agree without even thinking about it.

We headed back into the house and walked over to Thomas and Michelle.

“So how’s it going over here?” Chris asked with a big grin on his face.

“Good!” they both responded simultaneously.

“I was going to run out and get some more beer, since we’re running low. Then Michelle and I were gonna talk,” Thomas said.

“You two lovebirds talk now, I’ll take care of the booze,” Chris said.

He started to walk away, leaving me standing next to Thomas and Michelle as the awkward third wheel, *again*. I thought about what I had told Michelle earlier and how I said I could thought I could be assertive with a guy if I liked him.

But before I had a chance to prove myself, Chris turned around and looked back.

“Do you want to come with?” he asked. “I mean, unless you want to watch the fireworks between these two.” He motioned to Thomas and Michelle.

“I’ve had my share of third wheel-ness for the day,” I said as I followed him away from my friend and her new beau.

Chris and I climbed into his car and I pulled up directions to the closest place that sold liquor on my phone. I dropped it in the center console and we pulled away.

As we drove, we chatted some more about how we were such good matchmakers.

“It’s ironic, I’ve dated one guy and here I am helping out my friend,” I said.

“I’m single, so I’m not much better off,” Chris added. After a pause, he said, “Are you seeing anyone now?”

“No,” I said, a little too quickly. I could hear my inner Wonder Years voice telling me to play it cool. That I should have waited an extra beat to respond. That I sounded desperate.

We hit a bump in the road and my phone fell to the floor as we pulled up to a stop light. We both reached for it and our arms rubbed up against one another as I grabbed my phone.

I immediately felt a tingling feeling shoot through my arm. I almost shuddered from how good it felt. It must have shown on my face because Chris let out a cute little chuckle.

I was pretty much hooked at this point.

We went into the store and he bought whatever beer was on sale. As we loaded it into the car, our arms touched again and I felt the same feeling.

I thought back to my advice to Michelle earlier. I looked over at Chris and as he dropped the last box into the trunk, I leaned in and kissed him. It was like fireworks.

Obviously, I took him by surprise because it took him a second to start kissing me back. Within seconds, we were full on making out in the middle of the parking lot.

It had been years since I had even kissed a guy and my body was in overdrive. I didn’t want it to stop, but after what seemed like an eternity (but was probably like 30 seconds), we broke apart and got back into the car.

“Well, that was…unexpected,” he said. Uh oh, I thought. Had I misread his signals? I’d never just jumped a guy like that before.

“In a good way, though,” he added quickly.

He leaned back over and we started making out again. My body was in control and my brain was just along for the ride as we kissed. He was only the third person I had kissed, but he was by far the best.

I don’t know why I said what I said next, but the words just tumbled out of my mouth before I even processed what they would mean.

“My dorm room is like a block from here…”

“Let’s go,” Chris immediately responded.

We managed to keep our hands to ourselves as I showed him where to go. The entire time we drove to my dorm and walked up the stairs to the third floor room Michelle and I shared, my heart was beating a million miles a minute.

Once we got upstairs and into my dorm room, we were all over each other again.

After a few minutes of heavy making out, I stood up in front of Chris. My mind was whirlwind of thoughts. I couldn’t believe I had brought him back to my dorm room.

I couldn’t believe that I listened as he asked me to take off my dress. But I did.

I lifted the sundress over my head and tossed it aside, trying to be casual about it. I was still wearing my bikini and I felt a pang of self consciousness as his eyes looked up and down my body.

There was a brief second of panic as I realized that I had only been naked in front of one other person before. But as I looked at him, I could tell from the look on his face that he liked what he saw.

Like I said before, I’m relatively confident in my body. I think I look pretty good but it was still quite a feat for me to be stripping down in front of someone.

I reached around and untied my bikini top, letting it fall to the floor. His eyes grew wide as he saw me topless for the first time.

I figured I had come this far, I might as well let him see everything…I reached down and untied the sides of my bikini bottoms, letting them fall to the floor. I was completely naked.

I just sort of stood there, frozen in a Ricky Bobby moment, unsure of what I should do with my hands. Then I realized that I wasn’t exactly expecting anyone to see me naked, so I hadn’t shaved my pubic hair in…well, it had been a while.

He raised an eyebrow and nodded at my crotch. “I see you’re a fan of the 70s look.”

We both laughed as the tension drained from the air.

“I guess it’s my turn now?” he said. It was half statement and half question. I nodded in approval and he pulled his shirt over his head. He wasn’t toned or anything, but he had a nice, flat stomach and a nice hairy chest. He had a very sexy treasure trail from his belly button down into his shorts.

I imagined my hands running through it and how amazing it would feel resting against it when we were all done doing whatever we ended up doing. My heart was pounding in my chest.

Then I realized I didn’t have to imagine it. I summoned my courage and walked toward him. I reached out and slowly ran my hands through his chest hair. It felt so soft and warm. I’m pretty sure I let out a whimper.

I looked up at him and he chuckled again. “That tickles,” he smirked.

I ran my hand through his chest for a few more seconds and then slowly started moving my hand down his abdomen toward his waistline.

Before I could make it to the top of his shorts, he grabbed my hand.

“Not yet. Go sit on the bed,” he said as he motioned to the bed behind me. I slid onto the edge of the bed without hesitating. I sat there looking up at him as he took a step toward me.

Then his pants were on the floor and I was looking at the second naked guy I’d ever seen. No offense to my first boyfriend, but the difference was like night and day.

He had a nice, black patch of pubic hair and a big, heavy pair of balls hanging down. His uncut cock was…there’s no other way to describe it besides massive. I let out an audible groan of excitement and worry.

My first thought was, “*Wow. That thing is massive…*” followed immediately by “*There is no way that thing can fit inside me!*”

I managed to take my eyes off of his cock for a second and looked up at him. He had a goofy smile on his face. I guess he was used to seeing what must have been a look of complete shock on my face because he didn’t miss a beat before telling me, “Don’t worry, we’ll go slow.”

He stepped toward me and I knew what he wanted. Or at least I thought I did. Before I could reach up to grab his cock, he pushed me back onto the bed. I lay there, flat on my back, as he spread my legs open. I felt his hand on my thighs. The electric tingling I felt when we had bumped our arms together came back, this time shooting through my whole body.

I managed to grab a pillow from the top of the bed and shoved it under my head just in time to look down and see his tongue touch me. I gasped and grabbed the bedsheets. His tongue swirled around and I felt a dizzying pleasure. All I could do was move my hips in concert with his tongue.

Chris’ hands grabbed my legs and held them apart as he ate me out. It wasn’t until he had been down there for a few minutes that my brain was able to process that this was my first time getting eaten out by a guy.

It was everything that I’d heard and then some. I always thought women in porn were just writhing around for show but I couldn’t help bucking my hips as his tongue slid in and out of my body. As I did, his hands pressed me back down to the bed and held me there. Feeling him holding my hips down like that just got me even more excited.

Then I felt the orgasm coming. It was so much more intense than anything I had managed to give myself. I knew at the time was that *something* big was coming. I squealed in pleasure.

Later on, I learned it was a *full body orgasm* where your entire body is shaking and you can’t control it. I squirmed on my bed, writhing in pleasure.

My brain was just a cloud of fuzzy thoughts as I lay there recovering and breathing heavily. I don’t know how long I was stuck in the throws of my first major orgasm but when I rolled my head over to the side, Chris was laying there next to me.

He had a smug look on his face that said he knew he had not just a good job but a *great* one.

As the fuzziness cleared up, I managed to catch my breath. I sat up slowly and noticed the bed around my hips and crotch were soaking wet.

Somehow I managed to get up and make my way over to the sink outside the bathroom. I filled myself a glass of water and drank the whole thing in one gulp. My legs barely worked I had cum so hard.

I collapsed back on the bed on my side, facing Chris. I looked over at him and leaned in to kiss him. I slowly ran my fingers through his chest hair and down his stomach. This time he didn’t stop me as I moved past his waistline and through his pubic hair.

I reached his cock and realized that he wasn’t soft anymore. He was rock hard. I smiled and slowly wrapped my hand around it. I’d given my high school boyfriend plenty of handjobs before but Chris was at least twice as long and thick as my ex was. I could barely fit my hand around it.

I glanced down and moved my hand slowly up and down. A bit of precum lubricated things as I pulled his foreskin back and started to move faster. He groaned as I worked my magic on his cock.

I worked my hand up and down in waves, going slow and then building up to a nice fast pace before slowing down again. I enjoyed hearing his breathing follow in time with my strokes. I kept switching my gaze between his face and his cock. His eyes were closed in pleasure as he moaned. The moans were becoming more and more rapid but I didn’t want him to cum just yet, so I slowed down.

I let go of his cock and he opened his eyes, looking at me. “Something wrong?” he asked. I just shook my head and slowly climbed on top of him. I started kissing him passionately. His tongue slid into my mouth and mine into his. After a few minutes of battling, I broke away and slowly started kissing my way down his body. Past his chest. His waistline. His pubic hair. And then finally to his massive cock.

I wrapped my hand around the base and pointed it up in the air. I gently kissed the tip and he let out a moan. Then I started to take the head into my mouth. He let out a nice, guttural grunt as I did that. I gently swirled my tongue over the head of his cock before slowly pulling my lips away.

I started running my tongue all over his cock. I made sure to cover every inch of it before I made my way back to the head and started to take as much as I could into my mouth. I don’t even think I made it halfway down before I couldn’t go any deeper. Chris put his hand on the back of my head, not to force me deeper but to slowly guide me up and down as I sucked his cock.

After a few minutes, I felt his hand tighten it’s grip on the hair on the back of my head. I’d felt that same feeling before when I had gone down on my ex. I got ready for the familiar feeling of cum in my mouth. But Chris just pulled me off of his cock and let out another long, guttural groan of pleasure. He pushed me back and I slid onto the floor. He stood over me, his massive cock on top of my face. He gave it one or two strokes and then cum started shooting out of his cock.

A thick rope landed all over my face. Then another. And another. I had never seen a guy cum that much before, but it was everywhere. It slid slowly down by checks and onto my breasts.

I licked some up with my tongue and it tasted so good. I’ve always liked the taste of cum but his was especially good. I looked up at him and he had a look of pure pleasure on his face. His cum kept dripping down onto my breasts.

Chris looked around the room and grabbed a towel for me. I licked some more of his cum off of my face with a smirk as he handed me the towel.

“Not that you need it,” he said, handing me the towel.

As I wiped myself clean, he fell back onto the bed, completely spent. I climbed up to the top of the bed to join him and he kissed me on the forehead. I rested my head in his chest hair and enjoyed his heavy breathing.

We lay there naked for a few minutes, recovering before Chris got up and went to the bathroom to clean up. He came out a moment later and grabbed his shorts from the floor. He pulled his phone out.

“Uh oh,” he said, looking a the screen.

I raised a questioning eyebrow and he turned his phone toward me. It read “10 UNREAD MESSAGES FROM THOMAS”.

“I guess we got a little…sidetracked, didn’t we?” I said with a laugh.

“Yeah, I guess we did. Should we get back to the party?”

“Sure, but we’re just going to end up back here again, aren’t we?” I asked with a smile.

Source: reddit.com/r/gonewildstories/comments/brqo2k/fm_playing_matchmaker_has_its_benefits