HDD - First Time Candace Strays

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Candace cheats on her boyfriend with his best friend.
5.6k words
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Part 5 of the 9 part series

Updated 06/09/2023
Created 01/15/2020
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ENTRY 1

Hello virtual diary. It's Candace. Stupid. You already know that. This is my first entry and I feel stupid doing it. But I need to tell someone what has happened before I explode. I cannot tell any of my friends because it would completely change what they think of me. And under no circumstances can I tell my boyfriend.

You see, I am 19, a sophomore in college. I have been with my boyfriend, Daniel, since our junior year of high school. He is super smart and overall a really incredible guy. He and I are going to a really good college. All things point to him being a doctor. I am there on an athletic scholarship, one of the few given out to cheerleaders.

I went with him to this college mainly so I could be with him. I love him. He loves me. Say it again Candice. I love him and he loves me. I need to keep saying that. Anyway. His parents love me. My parents love him. They are really happy and supportive of us. They trust us together. I have pictured us getting married and having a family a million times. You get the idea.

He and I have had sex. Many times in fact. I always thought it was good. Maybe as good as it was supposed to be. Well... that was until a couple weeks ago. Let me start at the beginning and fill in details along the way.

Daniel and I were invited to the wedding of one of Daniel's friends from college, a fellow future doctor. I told him I would go if he planned all the details. I focused on getting a new dress and shoes for the event.

Well, the event was a couple weeks ago, where the incidents happened. That's right ... multiple incidents. I still can't believe it happened.

The wedding was a few hours from where we live so we decided to get a hotel. We left early in the morning and made the drive. We checked in and needed to get ready for the wedding. Daniel kept interrupting me as I was trying to get ready. As you would expect, it took him 10 minutes to get ready and me... well ... I need longer than 10 minutes.

The wedding was to start soon and I told him we did not have time to have sex. He kept flirting and touching me. He would see my standing there in my thong and bra in the bathroom putting on my makeup and he'd come up behind me and rub my ass. Then he would squeeze both of my big breasts with his hands. We did not have sex but I sure wanted to. I told him we could hook up after the wedding.

When we went down for the wedding, I heard a bustle off in the corner. As Daniel and I went to investigate we realized that it was Chet, Daniels best friend. As I found out later, Chet was invited, but was not sure he was going to make it. Therefore he conveniently neglected to mention it to us.

Let me tell you about Chet. He is a gorgeous, well built, hunk of a man. He is probably six foot three with well-sculpted arms. His chest has short hair all over it. I know because he shows off his six-pack abs and well-defined chest constantly. Any girl would be attracted to him. But he is usually a dick. In fact, he's always a dick. He doesn't give a shit about anyone but himself. He uses his good looks to be a womanizer. And no one knows how he is going to make a living, even him.

For the almost 4 years Daniel and I have been dating, I have asked him why they are friends a million times. I mean they have nothing in common.

He always reminds me that they have been friends for their entire life... that his parents used to babysit him, etc, etc. That is no reason to stay besties with someone in my opinion. Especially if he is an asshole and takes the friendship for granted.

Anyway, he still lives in the town they grew up in, two hours away from us. They see each other once a month or so when we go home to visit each of our parents. He and I try to get along, but mostly we avoid each other thankfully.

Anyway, for very minute I have known Chet, any time I am around him, he has constantly flirted with me. He tells me that I should be dating a real man like him. Ha! Like I ever would. I would never date a dog like him. What kind of terrible future would I have with Chet? I have the perfect future lined up with Daniel.

Chet still flirts with me constantly anyway. He has grabbed my ass a hundred times or more. He constantly looks at my big tits and stairs at me lustfully. When I mention something to Daniel he just says 'Chet is innocent. He would never do anything with you because of me.'

Whatever...

Anyway, I was not happy that he was at this wedding. I was hoping to have a romantic weekend with Daniel. Get him thinking about our own wedding. Now he is going to be distracted by Chet as usual.

Once Daniel saw Chet, they embraced as if they had not seen each other in years. And then they just talked and laughed. I decided to leave and go find a beverage.

Around 30 minutes later we were called to attention for us to take our seats. Chet decided to sit next to Daniel. I was surprised Chet did not bring a date. He mentioned he decided to come spur of the moment and that his first 10 choices did not have time to get ready. Dog!

The wedding was beautiful, even if Daniel did not pay attention to it or me that much.

As the newly minted bride and groom headed out to the ceremonial car to take them away for pictures, Daniel walked off with Chet. This day was getting better and better.

Maybe an hour later, Daniel made his way back over to me, at the drink counter again.

I made the comment to him, "Glad you could make it back. I thought we were going to spend some quality time together, in between the wedding and the reception? Remember you got me all hot and bothered while I was trying to get ready?"

He apologized saying he would make it up to me.

Then he had the audacity to ask for a favor. Listen to this. He said, "Hon. I have a huge favor to ask of you. I would totally be in your debt big time."

Reluctantly I asked what it was.

He said, "Chet did not have time to try to find a place to stay before he came to the wedding. We went to the front desk to see if there is a room available here and they said no. We went to the one next door and they are full too. Apparently we are not the only wedding here this weekend."

I knew what he was going to ask so I just answered, "No. I don't want Chet staying with us. This was supposed to be our weekend and so far you have spent every minute outside of our room with him."

He replied with, "Hon. Please. He has nowhere to go."

I reminded him that we only have one bed!

He replied by saying that Chet would be willing to sleep on the floor.

After a long pause where I glared into Daniel's pleading puppy dog face I finally gave in. "Fine", I said.

Daniel ran off to tell Chet the good news. I drank more. This weekend was turning into a disaster.

Finally the reception got going. Daniel did leave his best friend long enough to dance with me a couple times. When he got tired, Chet said he wanted to dance with me.

As we danced, Chet thanked me for letting him stay with us in our room.

I nodded and kept dancing. I was determined try to have some fun.

Three songs in, the DJ switched over to a slow song. I went to leave the dance floor and Chet pulled me back in. He put his arms around my waist and pulled me in close. I could feel his strength and smell his cologne. It was nice. Don't tell him I said that...

To play the part, I wrapped my arms around his neck and we danced. I am decently tall, especially with heels on. But I still had to look up to talk to him.

He looked down upon me and told me I looked wonderful. I said thanks. He continued to tell me that the dress showed off my wonderful ass. He reached down and squeezed both of my ass cheeks. I looked over toward Daniel to see if he saw. There was too many couple in the way.

Chet went on to tell me that the dress was low-cut and showed off my wonderful tits. I told him if he grabs my tits for emphasis that I would slap him. He just laughed.

When the song ended I broke his hold and sped off the dance floor. A few minutes later Daniel and Chet headed off to get drinks.

I sat there, at a wedding reception even more unhappy.

Chet finally went to the bathroom and I had a chance to talk to Daniel. He started by telling me thank you for letting Chet stay with us tonight.

I had forgotten about that. My quick response was, "Can you convince Chet to hang out at the reception for a while so we can head back to the room without him and have some fun?"

Daniel smiled and said, "Yeah sure. Let me find him and talk him into it."

Daniel jumped up and headed out to find Chet. I sat there thinking that maybe something positive was going to happen after all. That maybe I could at least get some sex out of the evening.

What seemed like hours went by before Daniel returned. "Where have you been?" I inquired.

He told me that Chet hooked up some whiskey and that he had partaken. I could smell it.

So I asked if was still interested in going back to the room.

He said yes and that Chet has agreed to stay behind for a while.

We headed back to the room and barely got into the door before we were taking clothes off and climbing into bed.

We made out a little bit. Daniel sucked on my nipples; which usually sends me to the moon. My nipples are sensitive and get rock hard when I am turned on. But it did not last long as I think both of us wanted to get to the act. Daniel put a condom on like he always has, and we started to go at it. I climbed on top of him and slid him inside me.

Daniel is average size, so I hear. I have not seen any other dicks. Daniel is the only guy I have ever been with. But I've always enjoyed sex with him. Remind yourself Candace... you've always enjoyed sex with Daniel.

That night, I was so hot and horny that he slid right in. I rode him up and down, pushing him as far in as could. I started grinding him hoping to get myself to an orgasm. He reached up and started playing with my tits; which he knows I love. I am telling you, they are like sex buttons.

This lasted for a few minutes before Daniel started to lose his erection. When he was almost completely soft, he fell out of me. I climbed off and asked him what was wrong. He said nothing, that maybe he needed to be in control.

Weird. That has never been the case before.

So he moved me over on my back. I spread my legs and he climbed in between. I reached down and guided his partially erect tool toward my wet pussy. He tried to push in but it didn't work. So he took over. He tried over and over and eventually his manhood was completely limp. The condom fell off.

Daniel crawled off and lay next to me. I asked him what happened. He rattled off excuses like he was tired or that the whiskey hit him. He closed his eyes and within minutes he was out.

Fuck.

Now I was pissed. I had been waiting all day long for us to be together. I had been horny for hours dreaming of getting off with my boyfriend and now he tapped out. I pulled the covers back adjusting Daniel so I could pull them out from underneath him. He did not even stir. He was quite unconscious.

I laid on my back and starting rubbing my pussy. With my left hand, I started tweaking my nipple. I was determined to give myself an orgasm.

As I worked myself up, I could feel myself getting close. I started frigging my pussy harder and flicking my nipple faster. I felt my orgasm approaching.

And then the door jiggled. I could hear Chet trying to get in. I stopped doing what I was doing and ran over to the suitcase and grabbed the first shirt I could find; which was Daniels. I put it on and ran back to the bed and jumped in. I pulled the covers up and closed my eyes. My plan was to act asleep.

Chet finally opened the door and rumbled in. To his credit, he tried to be quiet. He quickly headed to the bathroom. As Chet did whatever he was doing in the bathroom, I laid there fuming that I did not get my orgasm. I was so close! Now I was screwed.

I angrily decided to try to get some sleep.

I don't know how long it was after, but I felt a jostling of the bed. I was unsure whether it was Daniel or Chet or what. I was too tired to care. I tried to go back to sleep. But I was cold so it was difficult.

I lay there half out of it somewhat conscious of being cold hoping for morning to come as soon as possible. I don't know how long I laid there but it seemed like forever. Chet slowly made his way over to me. Gently he pushed himself up behind me connecting the length of his body to mine.

Because of my lack of consciousness, I was mildly aware of something happening, but was not recognizing the specifics. The thing that affected me the most was suddenly I was very warm. Chet gently wrapped his arm around me and pulled in tight. Feeling this comfort, I fell asleep almost immediately.

I am not sure how much time passed. But at some point, I thought I felt someone gently squeezing my tit and periodically grazing my nipple through my shirt. I thought I was having a sexy dream.

The person I thought was in my dream started focusing on my nipple more and more. The constant attention caused them to rise. My erect nipples are incredibly sensitive. With each flick, a small surge would rush right to my pussy.

This lasted for a few minutes until my dream partner moved over to my other tit. As attention began on that one, I felt like I started to wake up a little and realize that it was not a dream. I realized that someone was actually playing with my tits in real life. I was groggy and half asleep so the fact that it was Chet still escaped me.

Chet moved down and slid his hand under my shirt. He rubbed his hand over my bare breast stopping only to circle his finger around my hard nipple. Quickly he transitioned to pinching my nipples sending stronger surges down to my pussy.

I stirred a little and started to recognize what was happening. I started to take inventory. I really did have a hand massaging my breast and tweaking my nipples. This was causing my pussy to ache. I had a quick recollection of my missed orgasm earlier.

I became aware that it was in fact Chet doing this and not my boyfriend. I felt the warmth of his body. I felt his erection grinding against me. Even though I think he had shorts on, I could feel that he was big and rock hard.

Now that I was awake enough and aware that it was Chet, my first thought was that I should stop him and that I should slap him and kick him out of bed. That maybe I should wake up Daniel and tell him what is happening.

But I didn't.

I was fucking horny and unsatisfied. I had been for hours and hours. My pussy was on fire. I wanted an orgasm. And I was angry with Daniel. I blamed him for my current dilemma. If it was not for him, Chet would not be here and Daniel would not have drank and we would have had great sex earlier. I would be satisfied already.

I wondered if I let Chet continue playing with my tits, if I could have an orgasm.

I groggily adjusted how I was laying so I could give him more access to my tits. He moved back a little and I almost completely rolled onto my back. Chet sat up on his elbow and leaned over. My eyes were closed so I did not see him approaching. His mouth touched my nipple and I gently jumped. He flicked his tongue and my eyes rolled back into my head.

I started concentrating so much on the feelings coming out of my nipple, hoping for an orgasm, that I did not realize what else was going on.

Chet slid his hand down my pelvis and my legs unconsciously fell open. His middle finger slid over my exposed clit and into my pussy. He swirled around gathering some lather and then back to my clit. He rubbed my little nub in a slow circular motion.

I thought for a split second how wrong this was and that I should stop it right now. But a small moan betrayed me. My body betrayed me. I prayed for an orgasm. I focused on the build up in my pussy and Chet's mouth on my nipple.

Chet pushed his hand back down to my wet hole and slid two fingers inside. I was so wet they slid in easily. He pushed them in and out several times before pulling them back out and resuming his attention on my clit. It felt amazing. Daniel had barely paid any attention to me all night and here I was about to have my long awaited orgasm.

He increased the pace on my clit and lined his cock up to my wet entrance. I leaned back to protest and he kissed me. At first I was hesitant. My mind was racing. Then I let his tongue into my mouth and our tongues danced.

I felt my orgasm building. I was in heaven. I wanted an orgasm so bad after all these hours of building. He pushed the head of his cock into my pussy. I broke the kiss to protest and a moan escaped my mouth instead. He rubbed my pussy faster. I felt my orgasm approaching. I wanted that orgasm. I lifted up and pulled off my shirt. I tweaked my nipples. I wanted that orgasm.

Chet pushed his cock in deeper. The sensation in my pussy changed and it diverted my orgasm. He pulled his cock out and pushed it back in again. Over and over he repeated this while still rubbing my clit. My whole body was on fire.

I rolled over on my side keeping my leg slightly parted. He kept his attention on my clit as he kept pushing more of his manhood inside me. He was so big. I felt so full. How much more did he have?

Finally, I pushed my ass against him trying to get him deeper inside me. At this point, I wanted him to fuck me. It was too late to turn back now.

He pulled his hand from my clit and grabbed my hip. He thrusted his hips forward over and over pushing himself deeper and deeper. Chet was much bigger than Daniel. I felt like my pussy was going to be split in half. But my body loved it. My body was responding to it. My orgasm was so close. I wanted my orgasm.

Chet fucked me. In and out he went. I felt my orgasm hovering right there, ready to explode. It was stronger than ever. I tried to be quiet, but I couldn't help it. I moaned. As my orgasm came forward, I bit the pillow.

When it finally erupted, it hit me hard.

My pussy spasmed. Shockwaves shot through my body firing out my fingers and toes. I bit the pillow trying to hold in my scream. Chet kept fucking me. Every time he pushed in, another wave of pleasure would explode throughout my body.

Then I felt it. He pushed in deep and did not pull back out. I felt his cock pulse. I swear I felt a cannonball go down the length of his cock and fire into the depths of my insides. Over and over I felt his cock unload and my insides get coated.

This new sensation sent me into another orgasm of my own. Together we came. It must have lasted for an hour for it took a long time before I let the pillow go. He loosened his grip on my hip. I could feel his erection finally diminishing.

As we lay there intertwined, coming down from our orgasmic bliss, it hit me. I had just cheated on Daniel, with his best friend, who I don't even like, when he was right next to me.

Oh shit. I also let him fuck me with no condom. For the first time in my life, I had unprotected sex. Daniel and I never had unprotected sex. I am not sure what he's worried about. My mom put me on the pill years ago to regulate my periods. And we were both virgins when we started having sex.

My mind raced. Chet's softening tool is still wedged inside me. Fuck. I had unprotected sex with Chet and he came inside me. What was I going to do?

I had to get this event over with. I needed to get up and away from Chet. I needed to close the book on this one and never look back.

I reached back and pushed him back. When he slid his cock out of my sloppy pussy, he left a trail of cum down my ass cheek. I awkwardly crawled out of bed and headed for the bathroom. With every step, cum would leak out of pussy and run down my leg.

I barely glanced at myself in the mirror as I headed for the toilet. I sat down and pushed. I heard a big dollop of cum hit the water. Then I peed.

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