Cheekycheeks

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Gender: Straight Male
Age: 24
Relationship Status : Not specified
Profile Visits : 263
Number of Comments : 7
Number of Confessions : 0

Cheekycheeks's Favorite Confessions:

Out Of The Park

I grew up known as “the trailer trash with the big tits”. I wasn’t ugly or fat or anything. Blond hair, blue eyes, 5 foot 6, and had 34G bra before entering high school, you’d think everyone would want me. However, I was poor, couldn’t afford the expensive clothes and accessories so I was picked on a lot. The girls were probably jealous, I told myself. It didn’t matter. It was senior year and soon I’d be out. Or at least that’s what I thought.

I caught glances from the r******s in the park. They’d flirt with me but it was harmless. Except one who was kind of creepy and would make me an offer when no one was around. Nothing too bad. He just wanted to see my tits and feel them up and have me jerk him off. We’d go into his shed and I’d let him see and play with my tits, suck on them a little, then I’d undo his jeans and reach in and jerk him off in his boxers. I’d be lying if seeing his face as he was orgasming and then feeling his load cover my hand wasn’t a turn on.

It wasn’t long before he had me give him head. It was the first time I did it so he instructed me. For this he was sitting down and I took to it. It was the first time I saw it as when I jerked him off I never took it out of his pants, just reached in and did it. I could tell he was a bit on the thicker side but that was it. Once it was in my face I could say it was definitely thick and then some. I did my best with it. When he came he held the back of my head but made me keep eye contact as he pumped into my mouth. Seeing the pleasure on his face as his throbbing cock spilled his seed into my mouth that without thinking I swallowed down really turned me on.

Soon I was basically his. He had a girlfriend but she didn’t live there and after a couple months when I finally gave in and let him fuck me, he ended it with her. He told me right after he finished. His cum was all over my stomach, my belly button was full of it, and up between my tits. He really let loose, but was always a big cummer. He was wiping his cock off on the inside of my thigh when he told me after he ended it with her I was to move in with him. He was 42, I was 18. It took him about a month but he kept having me on the side until she was gone. Then that week I moved in. My mom enjoyed her booze and stuff too much to care.

I was basically his sex toy for the next 3 years until I moved on. I’d like to say it ended amicably but I left him for another older guy who I’m still married to to this day. Me 44 and he 67. In the end I made it out of the trailer park.

Does My Husband Like Me Cheating On Him ?

My neighbour caught me cheating on my husband with a delivery driver and now fucks me almost every work day.

Because the package was large, the delivery driver brought it in for me via our conservatory. He made a remark about me being a very good looking milf and minutes later I was knelt on our wicker sofa in the conservatory taking his cock from behind after I'd sucked on his young dick for a while.
Only my neighbour Henry saw me having sex.

When I saw him watching I thought my neighbour would definitely tell my husband, so as soon as the driver left, minus his cum filling my pussy, I got dressed and knocked on my neighbours door.

Now you would have to see Henry to understand why he wasn't exactly my type of man. For one he's fifty seven and trust me he's not the best looking guy.
But and it's a very big but as I've found out, Henry has a massive cock.
It's literally twice as long and twice as girthy as my husbands cock.

Henry's smile when he saw me stood on his doorstep was very mischievous and I knew then he'd want sex. Rather than go back and forth trying to get him not to say anything, I asked my neighbour if he'd like to copy what he'd witnessed.

I'm not kidding you, as soon as I saw his cock in his lounge I was on my knees greedily sucking on it.
As I've said Henry is no Adonis, but that afternoon with our neighbour fucking me for nearly an hour, it was easily the best sex I've ever had.
I swear by the time I walked a little shakily on my feet to our front door, I'd orgasmed multiple times and with a little help from Henry tonguing then using hair conditioner, I gave up my rear hole to him as well.

It's been three months since that first afternoon with Henry and I'm absolutely besotted with him and his huge cock. Plus Henry has a libido of a teenager. In fact it's me who sometimes has to take a break from being fucked by his massive penis. And even then he likes me to suck him to completion.

The other day however and the main reason im here, as I rode Henry's cock with him sucking on my breasts, his front door bell chimed. Henry answered the door after the door bell had been constantly rang.
I was still naked when Henry walked in closely followed by my husband.
All he said was "Now I know" and walked out.

My husband hasn't changed towards me one bit. In fact in the last few days he's cuddled me more and even gone down on me knowing I'd earlier had sex with Henry.
His only comment has been "I believe he's got a big one". And that's it. Nothing about me cheating on him, or anything about our marriage ending.
I'm not going to press my husband on it, but then I'm not going to stop having sex with Henry either.

I Lost My Virginity To A Woman Old Enough To Be My Mother

I was laid off looking for a job. I got a temp job helping with a budget. The Controller was a middle aged woman from India, dark complected but pretty. The work I was assigned was tedious. As the day turned into a week she stopped by to compliment me, having caught on so quickly. It was after hours and the door to the office I was in was closed behind her. She stood over me, shifting from one foot to another. She saw my eyes focus on her heavy chest and asked me if that was the way I looked at my mother.

She embarrassed me, leaned down and asked me if I had a girlfriend. I said no, and she pouted, poor boy you must be backed up now, do you need relief? With that she pulled the other chair and sat in it and rolled up to me. Let me help you, clear your mind a little. She bent down and blew me to completion. Wiping her mouth she asked me if I was willing to give her some relief now.

She reached under her dress and dropped her panties in my lap. Lick me. I had no experience with a woman, she leaned back and let me lick her. Trembling a little she said fuck me and got on the desk and leaned backward. My dick hurt it was so hard, and it slipped in easily. I fucked her and came quickly. Naughty boy, she told me. Twice now you got relief, and you left me wanting. Get your skinny weenie hard again, this time fuck me and control yourself until you make me orgasm.

It took a while, she used her hands and mouth until she got me hard again and leaned back in the desk for another try on my part. This time she let her tits out, and I got lost in them. She came, first whimpers, out of breath 'keep going'. She came hard calling me a bastard. Once composed, she left and told me HR would call and let me know if I was needed for the following week.

The call never came.

Took A Chance

Before i married my wife and we were seeing each other I forced her sister to have sex with me. She enjoyed it but I caught her by surprise. You see my wife was married when we started dating. I was 24 she was 32 my wife has a twin sister who’s the time was single. Had married young and was recently divorced. My. Own wife and her husband at the time where having a Fourth of July party and my girlfriend wanted me to attended. It was a rather large party and we found a way for me to go. She had her sister pick me up and take me to the party. We like both of we would pretend to have drank to much and crash there. Then her sister my now wife and I could fuck around. Only difference between the 2 sisters is my wife is a little thinner. Her sister is probably 10-15 pounds heavier but curvy. Besides that everything else is the same. They even taste the same. It had been a few hours I got a little alone time with the married sister some kissing some fingers and her hands and a few duck kissing. We figured it would be late when most were drunk that we would have a chance to mess around. It was a pool party as well and her sister and my gf where in bikinis. I had a beer or 2 but my fake date thought I may have had more. I was really horny and around 9 or so some people had left and the 2 girls stayed in there bikinis. My fake date went inside not sure for what and I found my way to her. I found her in a back room on her phone. Sounded like she was arguing with someone so i decided to come in and pretend that it was her sister while on the phone I came up from behind and hugged her grabbing at her tits kissing her neck and sliding my fingers into her. She squirmed a little still on the phone I let my cock out and pushed hard enough that she fell onto the bed on her tummy I pulled her legs towards the end of the bed so her ass was hanging over the end of the bed and stuck my tongue between her cheeks and gave it a few kicks. She went to hang up but the force of my cock and I mean I shoved it in I covered her mouth she dropped the phone she was tight I slammed into her and let go of her mouth. I was so worked up that I knew I wasn’t gonna last. My girlfriend and her sister are tiny women. I mean they are 5 feet tall my girl maybe 120 lbs and her sister mayb 135 lbs. I felt her shaking and moaning I pushed her face into the bed and she let out a scream I kept pace and she calmed down i wanted her rear bad so with the quickness and her face still buried face down her choice I pressed my head and swore I heard a pop and in it went. I kept a steady pace let go of her head she came up and she couldn’t make a complete sentence I pumped away and told her I was going to cum. Couldn’t make out what she was saying all I heard was gibberish and I came. I just laid there on top of her. She actually rolled me onto the bed and climbed onto me. She then told me wrong girl but kept kissing me and licked my neck over and over. She fucked me one more time and shortly after we went back outside. No one noticed we where gone that long. My gf her sister came up to me and said her husband was sloshed. We snuck off and I got head I was so hard that she walks tasting her own sister I fucked her later that night her sister knew she was ok with it. I actually dated bd had both sisters living with me when I moved her sister in with me. She asked if she could come live with us. For about 2 years I fucked twins. We got married and she moved out. Her sister never remarried and on occasion we hook up. Between the 2 my wife is the better fuck but her sister is the more adventurous meaning she will fuck me anytime anywhere with anyone. My best friend and I have smashed her sister a few dozen times. I’d never share my wife but I share her twin.

The First Job

My first job when I was 16 was working at a grocery store liquor store in shady part of town. It was not the worst area but it was sketchy. My dad’s friend owned a bunch of these type of stores and his son was running one that they had just purchased. I knew Todd he was a couple of year older then me. Some had an 18 year old boss and me 16 with a license. As you can imagine it was the most fun you could possibly have. As long as we got the work done we could do buy anything we wanted. There where a few others working here but Todd and I where close because we knew each other for a while and we just got along. There were always these women and girls that would come in. The ones that wanted booze but where not old enough had a way they could get some. Todd made sure that he and I were always working Friday and Saturday nights. We both walked in the back a few dozen times as some rando girl was slurping or getting railed. After the intense fuck we would deliver the booze to the cardboard container and leave it in a box. It was awesome we get sucked and fucked and they still give us money for the booze. It was non stop and for the most part it was the same girls that always came back. I remember there was this one tiny Latina that I really enjoyed slamming because she was so small. I had fucked her about a dozen times and she came in one evening I took her in the back absolutely slammed her and I yanked her hair fingered her ass and ended up shoving my cock down her throat. We where probably back there for 20-30 minute. She left out the back and I went through the front with what she wanted. As I’m passing her car that’s parked by the bin I see a guy in the passenger seat. I have her ass a smack and she said stop that’s my boyfriend. She had no problem and he had no clue. She was my favorite one and well I ended up getting hooked on her and here I am 20 years later and she is a stay at home mom still absolutely gives me what I want and I tease her about how slutty she was for me. Some ass you just can’t give up. I have tons of stories that I will tell. One about a married mom of 2 with a husband. She couldn’t pay her tab so she would come in once a week and let us tag team her. She had one of the nicest asses that i have ever seen. It was the shape of a heart her husband found out she was cheating and there was a huge showdown. Emily the wife literally was in the store in her thong when he showed up. She stood between us separating us from fighting and she was only a thong. I took her in the back to get her dressed Todd went out front with the husband they came back inside and found me and Emily slapping skin. Her husband left her and she ended up working at the store with us. She swallowed and ate more cum then I have ever seen a women consume. I learned that a women’s body can take a lot of punishment. She ended up hooked on meth and we ended up letting her go. She was a totally different person when she left the store. The last time I fucked her I am desire to go and he tested. Il post more on her eventually

She Did It To Save Money

I listed a car on marketplace, listed it about $3k to high to account for low ballers. This woman, probably mid 30s, mother, a little chunky but actually kind of cute came to look at it. I wasn't trying to rip her off at all, but she offered just under what I was hoping to get out of it, and I of course played the "oh I don't know, its in really good shape and its super reliable. Has all the maintenance paperwork and everything." After some back and forth she said she'd suck my dick if I sold it to her for the price she offered. After confirming she was serious I countered with if she down to fuck I'd go another $500 down. Seems like an expensive piece of pussy, but I wasn't exactly needing to make top dollar on the car and I actually wanted to fuck her. She immediately agreed. No hesitation. Went inside while her friend who drove her over waited in the driveway, and she was eager to fuck. She was good too. Big ol mama titties slapping up and down as she rode me, let me finger her ass when I fucked her from behind, and she took my entire load down her throat when I wad done. After getting dressed she gave me the cash and I gave her the title. Before she left she told me she really needed some action like that and she gave me her number saying she would like to do it again. I'm definitely going to reach out to her and have another go. Going to try for this weekend.

I Fucked My Son's Friend

First time poster here. Figured I'd start off with a true story that happened a few weeks ago.

I hadn't gone out in forever so I got the urge to visit an old nightclub stomping ground. Around midnight, the crowd started to pick up and I stepped away from the bar to walk around. Feeling out of place, I entertained myself by exploring the closed off areas in the 3-story club. Rule breaking can be a thrill for me so I had no problem sneaking around the forbidden staff stairwells and passageways; they were easy to get into since the bar staff was distracted by drunken college students.

After an hour of snooping I was bored again. I decided to call it a night and go home. Before leaving, I decided to take a piss. On my way out of the ladies room, I saw a lone college student sitting by himself, texting on his phone. He was cute so I decided to say hello before heading out.

When I asked what he was doing all by himself, he looked up from his phone and spun the barstool around to face me. He smiled as we made small talk. There was something vaguely familiar about him but I couldn't quite put my finger on it. I asked his name and when he told me, that's when it clicked. Instantly, I felt embarrassed because I realized he was my son's best childhood friend who I hadn't seen in years.

Laughing, I asked him if he was EB. He was like, "Oh my God wait, why....." and started laughing. I covered my face with embarrassment and told him, "Oh my God, I'm so sorry, I'm G's mom. I haven't been out in forever and I came over to tell you that you were cute but then I realized who you were, and boy, you grew up SO fucking fine!"

He thanked me, saying, "Well, not to be awkward but you look fantastic, too." I blushed and asked him if he still kept in contact with my son. He said no, they hadn't talked in forever and that their friendship had faded.

Immediately, I started to wonder how kinky it would be if we hooked up. I had played around with the fantasy since my son's friends are college aged but never truly thought of acting on it. However, the temptation was sitting in my lap so I took advantage of the opportunity and cut right to the chase. Blushing, I asked if it would be awkward to make out. Without hesitation, he answered, "I mean.... I'm down if you are."

I told him to come with me as I led him down the stairwell I had explored earlier in the night. On the way down the stairs, I told him that he couldn't say a word to anybody we knew about this. He promised he wouldn't.

I took him into a dark closet on the bottom level of the bar where everything was closed. Once inside, we immediately started making out. After a minute of heavy kissing, he grabbed my ass and started breathing heavily. He was kissing my neck and things were getting hot. I could tell me wanted to grab my skin so I directed his hand underneath my shirt. I could feel him shaking as he grabbed my tits. He pushed harder into me and I could tell he wanted things to escalate. I directed his hand down my into my panties, which were soaking wet by this point. He started playing with my pussy and asked if I wanted his fingers on the inside or outside. I told him inside, and he slipped them into me. He rolled his fingers around according to my direction and I felt myself needing more.

As he fingered me, I reached for his belt. I told him I wanted to suck his cock. I got onto my knees right there in the closet and he grabbed my head and worked it between his legs. I was shocked at his huge size and I was dying to know what that would feel like in me. I could feel his thighs shaking and when he apologized for being nervous, I told him he should be because it was a wild situation.

He asked if I still had his number. I didn't. He pulled out his phone to show me that he still had mine from years ago and asked if he could text me so we could pick up where we left off. I agreed. We snuck back upstairs and laughed about what had just happened, then went our separate ways for the night.

The next morning, I got a text. Since I had a free house, I invited him over. As soon as he walked through the door, we started making out. On the way upstairs I asked him if he'd ever been up to our loft. He said probably but it had been awhile. I said, "Well, there's one room I know you haven't seen before" and I led him into the bedroom. We started fucking and I asked if he wanted to film it. He happily agreed so we took turns filming from different angles. During filming, I asked him if he liked fucking G's mom and made him repeat it back to me on camera. That's one of my favorite parts when I rewatch it. I think about all the staged pornos out there and how much hotter the real thing is. The nervousness and authenticity of it is thrilling. I sent him a copy of the videos. I hope he watches them often because I sure as fuck do.

And E, if you happen to come across this story and recognize it as your own: you've got mommy's number so be a good boy and use it.

First Time Finger At Movies.

Summer 84... My friend and I went to the local theater to go see Ghostbusters. Once we got into the theater we saw 2 girls we knew from town. So we went and sat over by them. The one girl Allison was beautiful and Ive been crushing on her since the third grade. So for 6 years she's been the apple of my eye. Now 14 she has developed nicely. Nice boobs and a beautiful ass. As we waited for the movie to start she asked me to come sit next to her while her friend asked my buddy to sit by her. As we chomped in popcorn and watched the previews, Allison grabbed and held my hand. I was so excited and I couldn't stop smiling. The lights went down and the movie started. Allison took my hand and rested it on her bare thigh. It was summer and she had these incredibly short shorts on. As the movie played she took my hand and started to rub her thigh with my hand. I was pitching a tent in my shorts. She then leaned into me and whispered in my ear "I want to kiss you." I turned to her and we started to kiss softly at first. The kisses then started to get deeper and more intense. The whole time she was holding my hand to her thigh. The more we kissed, the harder I got. She reached down and touched me and rubbed me through my shorts. No girl had ever touched my dick. It was awesome. She stopped kissing me and whispered in my ear "You're so hard!" I nodded to agree. Then she whispered "Touch me! Feel how wet I am!" As. She guided my fingers up the leg of her shorts right to her soaking wet pussy. I never touched a girl before. The whole situation was intoxicating. She guided my fingers up inside her as she began to ride and hump my hand. Allison was moaning and whimpering in my ear as she slid my fingers in and out of her tight peach fuzz covered slit. She bit and sucked on my ear until she said "Oh my God!" She was sweaty and winded as she slowly stopped fucking my hand. I asked "Are you Ok?" With her eyes closed, biting her bottom lip, she nodded then grinned with gratitude. Then she reached into my waistband and grabbed a hold of my cock and slowly jerked me off as she rested her head on my shoulder. It didn't take long to cum all over her hand. She kissed my cheek and got up and said "I'll be right back" she went to the ladies room to clean up. When she got back she put my arm around her and we cuddled together and finished watching the movie. After that we never got together again. Our freshman year of High School started a few weeks later and she was already dating one of the seniors. I will never forget that day in the movies. Every time I see Ghostbusters it takes me right back to the Lincoln theater! Good times!

Mile High Club With A Stranger #1

I had 3 previous experiences with the mile high club, all with girlfriends.

I was on a flight from Sydney to LA. I was about 31 at the time.
I got to my business class seat (company expense) and got comfortable and began reading a book.

A passenger dropped something on the seat next to me and said hello. I replied hello without looking up from my book.
She then began putting her suitcase in the overhead compartment. As she did her shirt lifted exposing her belly which I saw out of the corner of my eye. I turned to look and then looked up slightly to see a massive pair of tits. Then I looked up further and she was looking straight at me…BUSTED perving!
I smiled and asked if she needed help and she declined.
We made small talk as the flight got under way. We were both married, I lived in Sydney she LA and she was a Cisco Systems executive returning to LA.
At one point out of the blue I asked “Have you ever had an affair”. She was very surprised, waited for a few long seconds and replied “that is a very personal question to ask someone”. I blushed and apologised, she then asked why I would even ask that question. I wasn’t expecting that and blurted out “Because you have really nice lips and I was wondering what it would be like to kiss you.” She said she would have to think about that.

It got uncomfortable fast as a long silence ensued. I picked up my book and began to read. Then she leaned over and began to kiss me. Soft and tender then quickly becoming hungry and eager. She slipped a hand under my blanket and squeezed me instantly making me hard. I reached over and put a hand on her massive tits and she stopped me looking around saying someone will see.
Then we kept kissing and her hand was back under my blanket where she undid my pants and slipped into my underwear.
I put a hand under her blanket and undid her pants and slipped 2 fingers into her drenched pussy and then up over her clit.
Then a moment I will never forget.
She looked around, leaned over, pulled my blanket back and sucked my cock for about 30 seconds which honestly felt like 5 minutes. I looked around and one guy was watching intently, but no one else noticed.
She came up and I told her to go to the bathroom and I’ll follow her. She started to say something and I stared at her intently and said “go now”
She slipped down there and I followed.
We began kissing standing up and I removed her top and she dropped to her knees and began blowing me again. I remember thinking “I wonder what her husband would think to know his wife was in her knees in an airplane toilet blowing some guy she met a couple of hours earlier. That turned me on and I was about to come.
I stopped her and sat her on the closed toilet seat and it was my turn to go down
on her. She loved it.
We tried a few positions and I bent her over and fucked her from behind. Her massive tits swinging in the mirror was a sight to behold and I didn’t last long. I asked her where I could come and she breathily said “inside me” so I did.
We when back to our seats and only the one guy from before had noticed anything.
She asked me if I would tell anyone and I said my best friend (and now all of you!)
She asked what I would say and I told her in explicit detail which turned us both on and got us kissing again.
15 minutes later we were back in that same bathroom. We were all over each other and totally naked in no time. I sat on the closed toilet seat and she sat away from me and using the wall and sink and began fucking me. I began with my hands on her beautiful tits and then slipped my right hand down and began rubbing her clit. That really got her going and she began getting more into it.
The thing is she began fucking me harder and when she came down on my cock it would push my legs apart a bit and made my left knee bang on the side of the wall. I moved my left hand away from her breast and tried to prevent my knee from hitting the wall, it didn’t work. I rhythmic “thud - thud - thud” continued and she breathily said she was close.
I let go of my knee and pulled her hair and began nibbling her neck and she came hard which then put me over the edge and I came.
My first thought was redemption as she had not even got close that first time because I came so quickly.
My second thought was then returning to our seats.
Oh My God the walk of shame…..
Everyone knew, and I mean everyone as they stared at us as we walked back to our seats.
Some with looks of envy, others disgust, but most of curiosity.
We then settled back into our seats like long lost lovers holding hands and occasionally kissing. Later we cuddled and slept with her head on my shoulder.

In the morning we landed in LA and her husband picked her up from the airport. At one point she looked over and slipped me a smile. I smiled back wondering the state of her panties as 2 loads of my cum slowly dribbled out.

Punta Cana

About 3 years ago my parents and I went to Punta Cana on a vacation. It’s my parent’s favorite place out of country to visit. They only took me there once 3 years ago. We stayed at our resort most of the trip because doing much more made everything so much more expensive. I spent a lot of time with my parents to not be too alone but sometimes the alone time was nice.

One day they went to get lunch while I was by the pool. This guy I had seen who works there had been staring at me for the last two days we were there whenever I went to the pool. He worked behind the swim out bar. I went to get water from him but he offered me alcohol which I gladly took. We chatted for a bit and eventually the conversation got very sexual. His shift was also ending relatively soon. I told him what room we were staying at and texted my parents to see what they were planning on doing. They were going to shop for awhile so I told them I had a headache so I was going to nap. I left the room unlocked and waited naked for about 20 minute.

He walked in and when he saw me we wasted no time. He fucked me for probably half an hour but it seemed so much quicker. We had sex all over the hotel room, even on the balcony. He finally came inside me which scared me at first but the feeling and the thought was so hot I didn’t care. In hindsight, I was lucky not to get pregnant with how much he came and with absolutely no protection. He left pretty quick after and my parents never found out. I saw him a couple more times and flashed him but nothing more happened.

We are leaving next month for the same resort as a final family vacation now that I’m busy with college and soon will have too busy of a life to go on vacations. Part of me hopes he’s there so I can have him again but I know the chances are slim to none. I’ve thought about hooking up with someone else when he inevitably isn’t there but it was sketchy to even do that once let alone again