HDD - Candace Strays to a Threesome

ENTRY 8

Hello Digital Diary. It has been a while since my last entry. Why does that sound like a Catholic confession? Because in a way I guess it is. I am confessing. I really messed up this time. I always intended to be faithful to Daniel, my boyfriend. In fact I have been able to justify my other transgressions as ones that Daniel pushed me to.

Let's start with the very first time with his best friend Chet. I didn't even like him, didn't want him to go to our friend's wedding, and certainly under no circumstances wanted him to stay in our hotel room. I was planning a romantic weekend that would get Daniel in the wedding type mood. But there Daniel was the whole night begging me to let Chet stay in our room because he had no other options. Lo and behold, we drink, Daniel passes out, and Chet takes advantage of me.

Fucking Chet was a mistake. But afterwards Daniel continued to push me to spend more time with Chet so that we could become better friends. His reasoning was that if he and I were going to get married then Chet would be in our lives forever; that I should get to know him and get closer to him. Well it opened the door to the continued affair I have had with him since.

Now Chet being Chet included one of his friends once, his brother a couple times, and his female fuck buddy. There is an argument to say those were all mistakes of opportunity all brought on by Daniel's insistence on hanging with Chet. But laterally the responsibility for all of those leads back to Daniel. I have at least a justifiable argument, however weak it might be.

I have come to grips with the fact that I am going to keep fucking Chet and once in a while his hot friend Megan. But I drew the line there. There are to be no more. I love Daniel and I want to faithful to him.

This new one though... I mean I guess I can say that Daniel has told me that I should make friends on the cheerleading squad. And that's how this all started. Let me tell you a few things for context.

Daniel has been super busy with school and has not had very much time to spend with me, especially in the bedroom. When we do it, it is really good. Well, aside from Daniel's conservative and sometimes limited bedroom repertoire that always includes condoms and other stringent boundaries. Actually, let me be honest digital diary, in a head to head matchup Chet is better. He is bigger, more dominant, makes me cum more. You get the idea. He is my go to when I really need to get down. But the 4 hours round trip to see him is not something I want to do very often. Plus Daniel is an amazing person and I have dreamed our wedding and life together for years.

Let me continue with what happened. First, I am a freshman on the school's cheerleading squad. I am extremely fortunate to have a scholarship. Very few freshmen ever get one. It is because I have years of dance and cheerleading experience and I rocked my tryout. It has caused some angst with a number of other cheerleaders who look at me as the chosen one or competition for whatever future positioning they may want. Whatever. So making friends on the squad has been difficult.

So a little more than a month ago, I attended a social that the entire squad was invited to. There were tons of athletes there, mostly from basketball or football. It's a ton of man candy of you ask me. I will never understand why they put these things together if cheerleaders and players are not allowed to date. Nonetheless, here I was socializing with some of my cheerleader teammates and a few players here and there trying to have a good time. And out of nowhere, the captain of our squad, our head cheerleader, Tiffany, comes over to me and chats me up.

Tiffany is barely 5', a tiny girl. She is some asian/fillipino mix. She is loud and controlling. In terms of assets, she barely has any tits, but a more than decent ass. She is the type that will wear a thong under her outfit to give the guys a show. She is incredibly pretty, almost completely natural beauty. Anyway, she comes over and chats me up like she wants to get to know me. We talk for a while about my potential and how she wants to take me under her wing and help me be successful. After she leaves I felt really good about myself.

Over the next week she works with me before and after practice, she introduces me to some of the other seniors on the squad and invites me to a smaller party they are having at one of their houses.

So I go. I am the only freshman there. There are a dozen cheerleaders and maybe 5 or 6 football players. Almost immediately Tiffany brings me over and introduces me to one of the players. He is a handsome black guy with a great smile. "This is Reggie. He is the defensive captain of our football team."

We hang out for a little while and I notice how touchy feely Reggie is with Tiffany. He is rubbing her and running his hands all over her body and she giggles at the attention. She finally announces that she needs a refill and asks if we all want another. I told her that I would help her. While we are getting refills I comment that Reggie seemed very hands on. Her response shocked me a little bit.

Tiffany says, "Reggie and I are kinda dating. We are not supposed to, so it is on the down-low. If anybody asks, we're just fucking."

"You are fucking Reggie? That big dude? I mean, what is he 6'6" 250 lbs?" I asked.

"Yeah he is somewhere around that size. But Candace, he has a huuuuuge cock. And he is amazing in bed. Have you ever been with a black guy before?"

I laughed and said, "No I haven't. I think some of them are attractive of course. But I have a boyfriend."

She laughed and said, "I see. Well take this drink back to Reggie if you would and I will be back to you guys shortly."

So I took the drink back to Reggie and handed it to him. He patted the couch and asked me to sit next to him. I am not sure why I did. I guess I thought it was innocent enough or the alcohol was lowering my worry radar. Whatever it was I happily sat down next to him.

We continued to talk and he laid on his charm and his humor. As I laughed and talked to him I was not paying attention to how he was gently running his hands all over my legs and my ass. It finally clicked when he said, "Candace, you are hot as fuck. You're pretty blonde hair, fat tits, and sexy ass. You are a top notch piece of ass."

Even inebriated I was insulted. I got up and told him that I needed some air. Maybe 10 minutes later Tiffany found me outside. She asked me what was up. I told her what had happened and she laughed. I asked her why she would think it was funny that her boyfriend is hitting on me.

Her response floored me. "Because he likes you. And I like you." She leaned in and kissed me. At first it was gentle and exploratory. I think she was feeling me out. Again, I am not sure if it was the alcohol or what, but I kissed her back. Finally I broke the kiss and looked around self-conscious of who might be watching.

Tiffany giggled and asked if I would come back in and sit with her and Reggie. I was hesitant but she was quite pushy so I did. The rest of the night was a blur. I sat with Reggie and Tiffany and they both touched me and made me feel sexy. When I left the party Tiffany told me she was looking forward to expanding our friendship. I did not know what it meant at the time, and did not think too much of it.

Daniel was quite happy that I was making inroads with the team captain. He looked at it as an opportunity, "If the captain takes you under her wing then that sets you up for better opportunities in the future right? Like you could be team captain one day?"

I shrugged it off at the time. But for the next couple of weeks Tiffany took me everywhere with her and introduced me to everyone. The coaches started paying more attention to me. I even got an invite to run drills with the competition team. I started to see what Daniel was talking about.

Fast forward to two days ago. Listen digital diary, I want to make something very clear. I was naïve and allowed myself to be sucked in without keeping my walls up. When Tiffany kissed me, I thought it harmless. In the two weeks after that, she did not try to do it again. She was completely normal. So when she sat me down after practice two days ago and talked to me about my future and what I wanted to accomplish with cheerleading I went with it. I told her that I would love to be team captain someday and was willing to put in the work.

Tiffany's response was that I also needed to do the social aspects. I asked what she meant. She told me that I needed to be social and friendly to key important influential people. "Like who," I asked. "Me for one," she said with a devilish grin. "I can help make your cheerleading dreams come true. She put her hands on my bare legs, up high on my thigh. "But you need to be open to the things that I tell you that you need to do." I nodded my head. My mind was flashing scenes of me leading the squad out to the football stadium on game day and running all the drills. My head got big.

At the end of our conversation she leaned in and kissed me again. It was sensual and enjoyable. When she broke the kiss she commented, "I enjoy kissing you. I hope you don't mind." I nodded that I didn't mind. Though I was embarrassed to admit it.

She continued, "Hey. Maybe it is too soon. But I have a really big ask. I told Reggie it was too soon, but he insisted."

I looked back up at her with a confused look on my face. She continued, "You see. Reggie and I both have a fantasy of someone watching us... you know... while we do our thing...aaaaaand... we were thinking that we want you to be that person."

"Why me?" I asked, "You have lots of better friends than me right?"

"But I really like you. And Reggie really likes you. Please!"

"I don't know Tiffany. I mean I have a boyfriend. That seems a little inappropriate."

"Listen it would be a huge favor to me. I would be indebted to you. Do you know how valuable a debt from me is?"

I was hesitant. She could see it written all over my face. She said, "Listen Candace. I am not asking you to fuck Reggie. I am merely asking for you to be in the room and watch us and if you get turned on to show us you are turned on. It is a big fantasy of ours. You can do that right?"

I think glamour flashing in front of my eyes because I considered the past few weeks and how wonderful they had been. Then I considered Daniel's comment about letting Tiffany help me and if she owed me a debt then she would certainly do that. And I thought about how Tiffany had just finished saying that I needed to be more social and to do what was necessary to seize the opportunity. And this does seem harmless. In hindsight I was justifying what I knew I wanted to do.

"Uh... I guess... I will."

She grinned from ear to ear and leaned in and kissed me again. "Thank you Candace. Reggie will be so excited. Are you free on Friday night?"

I nodded. She replied, "Okay. So I there is another get together at the house and we can make our way upstairs after. Okay?"

I nodded again. She leaned in and kissed me again and then said she needed to go.

So here I am in the shower Friday evening getting ready for the party. I shave my pussy and get my body all ready. I rub lotion all over my legs, walk to my dresser to pick out some panties. I grab a tiny thong that is really sexy. I catch myself. I am going through the same motions that I go through when I am going to see Chet. When I know I am going to fuck and I want to be sexy. Why am I doing this now?

At that moment, digital diary, I should have shut down. I should have recognized the signs. But I didn't want to. So I pushed them to the back and covered them up with dreams of making my cheerleading future.

So I make it to the party and Tiffany finds me right away and hands me a drink. The crowd is mostly the same people that were there last time. Mingling was easier the second time. Reggie sees me and beckons me to the couch he is sitting on. He pulled me down next to him and said, "I hear you are joining us a little later tonight?"

I responded, "Yeah. I am going to help you two out with your fantasy."

Just then Tiffany came back and sat on the couch on the other side of Reggie. Our conversation was good. Reggie was his usual touchy feely self to both of us. Tiffany and I got up to get some refills on our drinks and she led me outside again. Once we were away from the others, she leaned in and kissed me. I accepted her as she pushed her tongue into my mouth. She pulled me close and rubbed her body into mine.

As the kiss broke I asked, "What was that for?"

She laughed and said, "I enjoy kissing you. I hope you don't mind." I didn't. It was quite nice, especially after the alcohol had me feeling good.

Tiffany continued, "I am so excited that you are going to join us tonight. Reggie has a huge dick and he knows how to use it. He makes me cum like a hundred times. It's going to be awesome."

We headed back inside and recognized that the party had started to wind down a little as the couples found they needed to be elsewhere. That's when Tiffany told me it was time. She grabbed Reggie and we headed upstairs.

As I walked into the bedroom, I saw that it was not very big. The room looked smaller because whoever's room this was had put in a double size bed and shoved a computer desk against the wall. Reggie kicked his shoes off and took his shirt off and lay down on the bed. The bed creaked as it was forced to support the big man. Tiffany indicated that I should get comfortable and sit in the office chair next to the bed. I looked around and there really wasn't any other option.

I left my sandals and my purse by the door and sat down in the chair. The first thing I noticed is that the chair was on wheels and reclined. The second thing I noticed is that I was a mere 2 or 3 feet from Reggie. He could reach out and touch me if he wanted to.

Tiffany commented to me, "Candace, I know we asked you here to fulfill our fantasy of watching us, but feel free to touch yourself or to participate in this however you feel comfortable."

Tiffany put her sandals and purse next to mine by the door. She stood at the end of the bed and looked down on Reggie and asked, "Are you ready big boy?" He smiled and nodded his approval. Tiffany pulled her dress over her head and dropped it on the floor revealing that she was only wearing a tiny thong underneath. Her tits were a big A cup maybe, but she had long erect nipples in the center of a small dark areola. She winked at me before crawling on the bed on top of Reggie.

She nuzzled his manhood with her mouth on the way up to his face where they engaged in some serious kissing. It was sloppy and interesting given the size difference. It was crazy to see such a tiny girl lying on top of such a big man. His huge hands wrapped around her ample ass cheeks and made them look small.

It wasn't long before he pushed her thong to the side and started rubbing her pussy and her ass with his fingers. A few minutes later he picked her up and spun her around 180 degrees. He ripped off her tiny thong like it was nothing and pulled her down to his face. He started eating her bald pussy and her ass like he was starving. His big mouth covering both of her sexy holes easily. She started moaning like a whore, "Oh fuck Reggie. Eat my pussy. Lick my ass. Make me cum."

We didn't wait long before she started shaking and screaming, "Oh fuck. I'm cuuuuming!" If I am honest, it was really hot watching him manhandle her tiny body and force an orgasm out of her.

After he cleaned up her juices he rolled her off of him and told her to suck his cock. I could see an enormous bulge filling out his athletic shorts. And getting a better look at his body, he was very well built and extremely sexy. I was attracted to him. I could feel myself getting wet.

Tiffany adjusted her position to pull his shorts down. He lifted up to help her. When she did, my eyes nearly popped out of my head. He did have a huge cock. It was bigger than any cock I had ever seen; which was Chet's at maybe 9 inches. This cock had to be 10 or 11 inches and thick. His balls were the size of tennis balls. He was a big bull.

"Amazing right?" Tiffany asked me. I realized that my mouth was hanging open. "I think it's amazing." She gripped it with her little hand and started stroking it. Soon she added a second hand and still only covered half the length. She leaned down and tried to put her mouth over his cock but could barely fit more than his head in her mouth. He reached up and pushed her down forcing some of his manhood into her throat. She gagged and he finally let her up. She gathered herself and then said, "Do it again."

They repeated the process causing Tiffany to gag over and over. Then she started looking at me. Every time she was recovering her air she would look at me. When he let her up this next time, there was a huge string of saliva connecting her mouth to his cock. She reached up and grabbed it and used it as lubrication to keep two-hand stroking him. Over and over they repeated this process. Before I knew it I was reaching under my dress and massaging my pussy. I was so wet my thong was drenched.

I watched him manhandle her and force his huge cock down her throat over and over and for some weird sick reason it turned me on. In between one of the sessions while Tiffany was trying to recover, Reggie looked over to me and asked, "Do you like this Candace? Do you like watching your friend try to please me?"

I joked, "She sure is trying." Tiffany looked at me and said, "You should come over here and try it Candace. I think he would love your sexy lips plunging on his hard cock."

I visualized myself trying to suck a cock that big. Part of me was frightened at the prospect of being gagged, but part of me thought I could do a better job that she was doing. But I tried to stay in control and responded, "Noooo. I don't think so. I am doing just fine over here."

Tiffany replied, "I see your hand in your panties. Why don't you get undressed and make it easier on your self?"

Then she went back to work, bobbing and choking, and gagging. I thought she had a point. They were quite naked and I did have my hand on my pussy. So I lifted and took my soaking wet thong off and laid it on the desk next to me and resumed my masturbation.

Tiffany, after recovering yet one more time, looked up at Reggie and asked him if she could climb on top of his huge rod. He nodded. She spit another heavy dose of saliva onto his cock and then moved herself into position. With her free hand she spit one more time and added it to her pussy before lining herself up. I was intrigued to see how this was going to work.

She slowly pushed the head of his cock through her small opening. He winced and her face contorted. She used her strong legs to control the distance as she slowly went up and down. She started rubbing her pussy hard filling her pussy with lubricant. It took a few minutes before she finally settled in. She had about half of his cock buried in her as she went up and down. Her moans could easily be heard outside of the room.

Reggie moved his hand over and laid it on my leg. His fingers reached into the insides of my thigh. If he stretched he could have touched my pussy. But he didn't move any closer even though my pussy wanted him to. I started massaging my pussy faster feeling an orgasm starting to stir.

Tiffany broke my concentration by yelling, "Oh fuck. Oh Fuck. Fuck me you big dick bastard. Oh my god." I could see her orgasm coursing through her body. As she came down from her orgasm I saw Reggie push his cock deeper inside of her causing her to curse some more, "Oh my god that's fucking deep. You are so big Reggie. You are going to fucking break me in two."

They fucked like this for a few more minutes before he lifted her off of him and rolled off the bed. He pulled her back over like she was a bag of potatoes and lifted her ass up in the air. His cock was huge in the dim light and his body was stunning. He was muscled from head to toe. Once she was set up doggystyle, he lined his massive erection back between her legs and pushed. She was facing me and I saw her face change from pain to utter fulfillment. Her eyes rolled back into her head and her mouth dropped open. She started moaning loud and reckless. I looked up and I saw Reggie looking back at me with my legs spread open watching me finger my pussy. Together we stared at each other as I reached a long awaited orgasm. Reggie just smiled at me as I finally calmed down and reopened my eyes.