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:

Work Wife

There is such a thing as a work wife. About 3 years ago the company I work for hired a jr assistant to help me out. Lynette or Net for short was a fire cracker. Perfect in every way work and physical appearance. Short at 5 foot 3 and 130 lbs she carried the weight she did have in all the right parts. Blondish hair hazel eyes perky boobs and a plump ass. It is a very nice ass.
We worked on 3 large projects right off the start and got to spend a lot of time together trying to meet deadlines. We temporarily moved her into my office while we worked on these projects together. I was not happy about sharing my office but after a few days it ended up being a good idea. It kept us on schedule and her choice of clothing was nice as well. Leggings that showed her plump ass or skirts that would show her nice thick thighs. Most days I worked with a hardon. Because of her ass I never really noticed how nice her boobs where into the 3rd day there when she wore a V neck sweater that showed how nice her tits where. They were visible and looked larger then when we first met.
We worked well together and got to know each other on a personal level. We would have lunch together most of the time we had it brought in to be able to work through the hour.
We both were very flirty with each other and always pushed the issue. She would walk by me while I was in our storage room and when she did she would put her back to me and always make it a point to have her ass run against my cock. A few times I felt her push her ass back. A few times i would stop her by grabbing her by the hoops and we would dry fuck each other. I finally one day while in our storage room looking for ink she came in and was wearing a dress that was knee high and was a 1 piece with straps and her tits spilling out of the top. She did the whole ass rub and i stopped her to grind a bit. I this time slid my hand under her dress and before she could say anything I had a finger in her with my other hand I came up and cupped her tit. We kissed and I slipped in 2 fingers. I pulled my finger out put them to my mouth and tasted her juices. I took her hand walked her over to my desk pulled my trousers down and had her sucking me off. She jerked and sucked until I blew my load in her mouth. She was a champ swallowing most and whatever spilled out she licked up afterwards. We kissed little more then turned her around and went down on her. I was hard again and this time I had her sit reverse cowgirl and did her while sitting on my chair. If someone would have walked in they would have seen Lynn goin up and down with her tits flopping around. We takes after and agreed on some things. Never on weekends unless we could do it with our risk. Never let it stop us from getting work done.
These simple rules has us working together for a little more then 3 years. Most of the staff has moved into a new office leaving her and I alone which makes it nice for the day fucking. The bosses are happy and were ok with me staying away from the hectic noisy office.
Only noise that we hear now is when I sticking it hard into Nets ass. She admitted that she had never had anal before. I am infatuated with her ass. She has said that her husband had always wanted it but said when they were first married she tried and it hurt so it was a no go. She said that the first time she did it with me it hurt like hell but wanted to make me happy so she went with it. She said besides you don’t really give me a choice. You just bent me over the desk squirted lube in my ass and stuck it in. 3 years later she takes it like a champ and has cum from it as well. Conference call bjs or she sits on my lap while we are on a call. Sometimes I eat her out. With her sitting in front of me on my desk with her legs spread open. Some times when we come back from lunch we have to air out the room. There is an odor that is hard to describe sweaty pussy and ass is the way I can describe it. We started early today to try and finish up a project and will be fucking Net shortly. I found that she likes it a bit rough. She cums hard when I grab her by the hair and ram it from behind. Age wise she is a bit older otherwise I would consider trying to knock her up. I truly can say that I love my job.

Can't Believe I Did This

I am 24 and my boyfriend is 23. A few weeks ago he asked me to if I would do something for him. He made it clear this would be sexual. I thought he was asking me to participate in a 3sum, which I didn't exactly object to. But he kept being vague and when he finally came out and asked I said "HELL NO".
He asked me to have sex with his 16 year old "VIRGIN" brother (Ricky)! He kept bugging me about and I don't know why but in a moment of weakness I said OK".
Last Saturday night came and I knew we were getting company. I shaved everything and put on a sexy matching bra and panty set. When Ricky arrived I was very nervous and didn't want to waste time, just get ot over with. I led him to the bedroom. Like I said Ricky is only 16. He is kind of a shy, skinny computer geek type. As for me I am not some swimsuit model. Tall for a girl at 5-9, pretty (I think), small B cup tits but a decent ass. When Ricky undressed I was impressed. He had a nice 7 inch cock and large balls. Actually bigger than his brother. We got on the bed and I slipped off my bra and panties. He was very eager. Kind of skipped making out, he went straight for my tits, licking and sucking. After a few minutes he moved down and I spread my legs wide to give him his first taste of pussy. I have to give him a "C" on pussy eating. I had to slow him down several times and point him in the right direction. Ricky finally raised his head and moved up between my legs. I sat up and intended to suck his cock hard but when I reached down I realized he definitely didn't need help. He could have chipped ice with that cock. I guided him to my pussy and laid back. Once inside me Ricky only had one speed. TURBO! He hammered away at my pussy on warp speed. It felt good I admit. He only lasted about 4 minutes when he began grunting and I felt his cum inside me. But Ricky gave me the surprise, actually amazed me! I expected him to get soft and pull out. But he didn't slow down, he just kept fucking!!! And he stayed hard! When I realized he wasn't going to stop I got really turned on. I started pulling him in for kissing, scratching his chest and back, wrapped my legs around him and started talking dirty. The sheets were soaked. I could feel his cum sloshing out of me as he fucked. He lasted longer this time but eventually came inside me again. He tried to keep fucking but I felt his cock finally going soft. When he pulled out I looked up. OH MY, it looked like someone poured a glass of milk all over his cock and balls! I sat up and looked down at my pussy. It was a white sloppy mess. CUM EVERYWHERE!
We caught our breath and cleaned up. Ricky spent the night in the guest room. My boyfriend was eager to get his turn when we went to bed.
When I got up the next morning Ricky was on the couch watching TV. I was dressed in panties and a t-shirt. I hesitated for a second but finally said what the heck. I walked over and got on my knees in front of him. I tugged at his sweats. Ricky responded by arching his hips and pulling his sweats down. I looked him in the eyes as I stroked his cock. Then went down and began sucking. His cock got hard in seconds! I could tell he really was enjoying his first BJ. I decided to give him a special treat. I went hands free. I slid his cock all the way down my throat and held it there. He was literally shaking! I came up for air, looked up at him and asked "did you like that". I definitely got a yes. I began massaging his balls and giving him deepthroat head. About my 3rd time sliding him in my throat he arched his hips and exploded. I couldn't imagine he had that much cum still left after the night before. I wasn't easy, little choking, but I swallowed it all.
The end... So far.

My Neighbor Growing Up

I was 12 when the new neighbors moved across the street. I went up and introduced myself and met C the wife and D the husband. They had one little one a boy 2. C was 27 and D was 25. He was gorgeous and I think probably for the first time my little pussy that was finally sprouting some hair got wet, I mean really really wet. I didn't notice as I helped them but I had soaked the crotch of my shorts. Walking back to my house I was holding my legs tight so no one could see. My older sister saw when she came into our room and I was changing. I explained about D.

They had a pool, and my family could come over uninvited and use their pool. It was really only used by my brothers and us girls, my dad had died a year earlier and my mom I think went over a couple of times, though she and C were getting to be good friends. At 14 I had a nice body, though only A cup boobs, I was a big embarrassed that they were so small. Once I was in the pool with D and he and I were just swimming around. He stood up against the edge of the pool I bent over into the water and as I came up, the weight of the water pulled my bikini top down and he could see my tits clearly. I pulled up my top and he told me how good I looked. I told him I didn't like them because they were small. He remarked that they looked to be the same size as his wife and had the same size and color nipples as hers. He said he like that type. With that I bent over again, and with him shielding me from the view from their kitchen window I let him seem them again. Within a minute I had leaned up again the pooside and in the water he reached down and pulled my bottoms down in back to see my butt. He told me how good it looked, and asked what else I was going to show him. He said that afterall he'd see me almost totally so we might as well make it fully. With that I turned around and pulled my bottoms down below my crotch so he could see my now fully brown haired bush. He reached down and rubbed between my lips and I felt like I would faint.

A couple weeks later, C was gone and when D and I got out of the pool, with more feeling and touching, this time I was touching him too. We went inside to change. I went into the bedroom with him and he tried to tell me to go into another room, but I wouldn't. I told him after all, I didn't have anything he'd never seen or felt before, and the same for him. We took off the wet suits and I went to him, arms around him and kissed him. I asked if I was OK for him totally naked finally with him, he told me I looked just like C, same tits, same bush on our pussies, and it was what he liked. I got to see her a few times, changing and she remarked that I should watch for D since I clearly was the type he liked.

He got super hard and I said i wanted him. He wouldn't do it, wouldn't even let me suck him. I wanted him so badly but he said i wasn't old enough. I started pouting and he held me, gently laid me on the bed and got on his knees on the floor and begin licking me. I came three times. Then he got up and pulled me up and we dressed. I asked to do the same to him and he didn't want me to do that, I asked if I could use my hand and he said we could, but later.

When I was 20, I went to work for D in his company. We were out in LA in a hotel. I had the room next to his. There was a terrible storm and I called to his room and begged to come over. He said he wasn't wearing any clothes and I told him I wasn't either. I was no longer a virgin but I still wanted him desperately, even though C became a really good friend. He unlocked the interlocking doors on his side, I did the same and walked in, crawled under the covers with him. That was honestly the best sex I've ever had, before and even now after. We shared each other for two years before I moved on to another job.

I am now 47, have three kids of my own, married for the last 19 years. I've grown fat, my husband is fat, and my mom moved in with us. On her birthday C and D came over to the house. He still looks incredible, and now I'm just a fat old mom. But I have the memories of the two years of incredibly great sex to remember. Before he left, I got him aside and thanked him. He returned the thanks.

I’m Am Lost

I work at a sports bar, where one night I found myself seating a party of 2. Unbelievably one of these jerks was my ex bf father. He called me a whore after I seated him, saying I was the reason his son became an idiot. I was highly offended. I went to the back, and emotionally panicked, cried my eyes out. I clocked out early that day and went home.

The next day I was furious and sent him a message. I showed up to his house and slapped him when he opened the door. He yanked me in and closed the door because I was shouting at him. I told him I never wanted to see his face at work. I was so enraged, he told me to calm down or he would press charges. I knew he was bluffing so I kept pouncing on his chest. Then he subdued me and told me he was sorry. He was huge, manly and felt like a strong bear holding me in. He the whispered into my ears he missed me because I was the only good thing he had going for his family. I was smart, educated, with a future. He was upset that I gave up on his son but he understood he wasn’t man enough. He wanted us to be successful and was enraged when he saw I was wearing skimpy clothing and working at a sports bar.

He ended up fucking me, in the kitchen and then his wife’s bed. It was the best pounding I ever had. I was so turned on, he choked me and kept calling me a classless whore while thrusting into me. I had missed text messages from roommates and my bf asking where I was. His cock was knocking the air out of me and sending shivers up my spine. I was lost in ecstasy, but something told me to secretly record when he was looking for a condom. I yanked it off mid sex and he fucked me primal and came everything he had inside of me.

He kicked me out when he saw his family was heading home. Told me to not show up again. I was a mess, but I checked my phone and I had him. I sent him the video right after and told him I was in control from here on. That if he ever wanted to keep his marriage he would do exactly as I said. I was on the pill but I didn’t tell him. When I met up with him again, I ordered him to fuck me making sure he kept cumming in me. Once when his son called me, and another when he was on the phone with his wife. For years I had a grip on him. I never told anyone, he helped me through college.

I feel guilty, I hate that my boyfriend doesn’t know but I fear he would leave me and I will be alone again. I lied to him so many times, when in reality I was enjoying the best sex from a man who hated my guts. I just wanted to vent, I put an end to it after college. Every-time I hear about my ex bf and his father I’m reminded of the violent sex I enjoyed with him.

Taking It Out With On Katie

My neighbors are in there mid 40s and are total pricks. Jay and Katie. Jay owns a company construction or something a long those lines

They always have complained about noise my friends hell even my dads hot rod. Seems like we would be super nice and they would just ignore or refuse to be nice.

As I got older I worked out and got in good shape. Friends would come over and we would work out. I found that Katie who is a strawberry blond around 5foo7 small boobs but has really thick thick thighs and bubble butt.
For being such a bitch she looked really good especially when she was in stretch pants tights yoga pants. Some times she sported some camel toe or you could see her undies through the thin fabric of her pants.

She was a lot nicer when Jay was not around. I figured they hated us so I would just be nice to be nice. Specially with Katie. I made it a point to talk with Katie when she was out front watering or cleaning her car. Always seemed to be when I was working out and had the garage open.

One day I just said fuck it and started to flirt. I had the house to myself my parents were out of town. I had been in my garage working out I figured why not they hate us already. I noticed that Katie was working in her yard pulling weeds. She had a mat down for her knees to rest on she was on all 4s with her big ass in the air. I walked up behind after staring at her for a minute I took a deep breath I stood right behind her and said damn Katie you’re looking really good. That position suits you. She was surprised and sat down and turns to look at me. She was beet red and I keep it going. I told her thanks for the show I really appreciated it. She didn’t say a war just stared at me. I told her turn around and keep pulling weeds. To my surprise she did. I dropped to a knee right behind her as she had gone back to picking weeds. I put my hand on her ass and started to pinch and run my hand between her cheeks. I pushed my hand hard between her cheeks felt how warm her holes were.

I told her to get up and to come with me to my surprise she got up and asked me where do I go. I said go inside the garage she walked a few feet in front of me and i told her to take her top and pants off. All she said is she she didn’t have a lot of time Jay would be home in a few hours.

She took her pants and top off and was standing in my garage in a bra thong and sneakers. I bent her over my weight bench and licked her ass and pussy. I spent the next 2 hours licking and fucking every hole she had. Jay called when I was balls deep in her ass to tell her would be home on 45 minutes or so.

I started pumping really hard and deep when she was on the phone with him. She did her best to not to make any noises but I could see her face on the mirror. I snapped a few pictures and recorded us. I had Katie hold the phone and take a bunch of selfies of us while I pounded her from behind and while i was in her behind. I blew loads in all her holes. I saved her mouth for last. I face fucked her after using her other holes.

She said she had to go. She put her pants and shirt on I kept her panties. I gave her a hard slap on the ass. I told her to text me a picture of her taking a shower later that day.

I have been taking it out on Katie for about 6 months now. She comes over to work out or I go over after Jay leaves for work. We have lots of videos and pictures of us having sex. I even took her out on a weekend date in another town while Jay was fishing for the weekend. She dressed super slutty and took her to some bars. For my 21st birthday she took me to a strip club and I got her to get on stage on dance for me and my buddies. After watching her grind on the pole I took her out to the car and pounded the shit out of her.

Jay has no clue that I use Katie as a human fuck doll. We discovered that she is a squirter and have told her that I wanted to see her and another girl go at it. Her response was if that what you want me to do then il do it. I just heard Jays truck leave so I’m going to go fuck her now

I Got Head Constantly Growing Up

I still think back on this and wish it was still my life, my cousin Stella and her mom moved in with my family when I was 14. She was 11. We sort of had already grown up together, her stepdad was a piece of shit and they spent a lot of time with us because of it. When I was 16, we started spending a lot more time together because I could drive us both to and from school, so we talked about anything and everything in the car. I found out when she had her first kiss and in the same night gave her first handjob. I didn't expect her to be so straight up about it and then she asked me if I ever had a blowjob. I said yeah and asked why? She said she wanted to give the guy one but was nervous what it was like. I described the kinds of things girls normally do, the technique, asked her if she wanted to watch any videos to see what it was like and she said yes so when we got home we went to my room and laid in my bed and watched porn on my phone. I got really fucking horny and started seeing Stella in a different light. She was touching her lips and moving them around and sticking her fingers in her mouth and I couldn't stop picturing her with a cock in her mouth. We watched some porn of blowjobs but some videos went into actual fucking and a few times I tried to change it back to blowjob porn she told me not to. She was 13 and barely had tits, but I could see her nipples poking through her tank top. We watched a bunch of different videos and I had been trying to think of a way to get her to suck my cock so I said "I normally never watch this much porn without jerking off, we can keep watching but I need to jerk off" and she said okay so I just took my cock out and started stroking it while we watched the video we were on. She stopped watching the porn and was just staring at my cock, still sucking on her fingers so I asked if she wanted to practice on me. She said it was too weird cause my face would be right there so I said she could put a blanket over me so only my cock is out and she can do whatever she wants with it and she agreed to that so she sat on the pillow and I laid down with my legs around her and my upper half under the blanket but what she didn't know is if i crossed my arms under the blankets it would create a gap big enough that I could watch her. She played with it with her hands for a long time, and her hands were so small they made my 7 in cock look like a footlong lol. She put it in her mouth eventually and I watched her try to do what the pornstars had been doing. After just a few minutes I told her I was going to cum and she stopped sucking me to jerk me off while I came, but then licked some of the cum off of my dick and sucked on the head for another minute.

After that it was all she wanted. We'd get in the car and she'd say "can I suck it when we get home?" because our parents weren't home, and I was getting sucked off every fucking day so I stopped trying to get with girls at school and was happy just getting blowjobs whenever I wanted one. She started masturbating whenever she would suck me off and would usually have an orgasm before I did. Sometimes she would suck me before school, it just became a constant thing she wanted to do and while the frequency lessened continued until I moved out for college. Now as adults if both of us are single and we get together we will always find somewhere to get alone but unsurprisingly we started fucking years ago so last night after her mom's birthday dinner I took her to the car where she sucked my cock and I pounded her into the back seat then sent her home full of cum.

I had been dating my girlfriend for about a year and we decided we wanted to have a 3some with one of my buddy's. Now my buddy had actually had sex with my girlfriend 3 years prior to us dating and I wasn't a jealous type so it didn't bother me. Now I have a small dick and I know that, it's about 4.5 inches and it's not that I'm not good in bed my girlfriend cums every time we have sex if not multiple times but I understand I'm not hitting some of those deep areas that someone with a bigger dick can hit. And the best way to keep your girl happy is to make sure she is totally satisfied and I told her this and she was surprised but loved that I'd be willing to let her have sex with someone else. She had told me before that the time she had sex with my buddy was honestly the best sex she's ever had so I told her we could have a 3some with him she was so excited of course. Now when the night came I realized quickly why the sex had been so good, my buddy had an 8 inch dick with a perfect girth and my girlfriend looked so happy being able to actually put her whole hand around a dick while she gave her amazing blow job. She is on birth control so me and my buddy both were gonna be hitting it raw but it ended up being less of a 3some and more of me watching my girlfriend get her brains fucked out from behind while yelling out stuff like "I missed this good dick so much" "I forgot how good big dick felt" "this your pussy now, you can have it whenever". And to be honest I understood why so I didn't make a big deal about it. The embarrassing part is my girlfriend fucks my buddy no less than 3 times a week now and she constantly sends me pictures of her face covered in cum and videos of her getting fucked. She laughs and tells me that's how a real man fucks a girl. And reminds me all the time during sex that I'm just borrowing his pussy and that he is daddy which turns me on knowing my buddy has literally stolen my girlfriends pussy

Fun By The Pool

I've read a lot of neighbor boy stories on here. Seems like there's one in every neighborhood!! This kid who lives next door he's like 13 or so always likes to spy on my when I'm swimming in our pool or laying out to tan. He thinks he's hiding behind the bushes on his side of the fence but I know he's there. I usually like to tan topless so I knew he's seen me seminude. A few weeks ago on purpose I put my chair right near the fence and swam a couple laps. After awhile I saw he was in his usual spot and I waited a few minutes then got out of the pool and walked over to my chair. I grabbed my towel, dried off, then laid the towel on the chair. While facing him I reached behind my back and undid the hook, and took off my bikini top tossing it next to my chair. Then I slowly slipped off my bottoms and tossed them next to my top. I stood there awhile completely naked, letting him get a eyeful. I had shaved that morning so he got to see my bald pussy up close. I took my tan lotion and rubbed some onto my arms, my breasts, stomach, and legs. Finally I sat in my chair and pushed it back so I could lay flat. First I was on my stomach for a few minutes, then I turned over and laid on my back. The foot of my chair was facing him, and after a little bit I turned over. Knowing he was only a few feet away and could see me naked up close was really turning me on! After a little bit I got more daring and parted my legs and pulled my knees up, giving him a straight on view between my legs. I closed my eyes and I guess I ended up falling asleep, because I kinda woke up and noticed he was gone. I smiled at the thought of him going inside to jerk off, or maybe he did right there when I was sleeping. Who knows, next time I might ask him to put some lotion on for me!

Finally Did It

My husband had taken our son to a tee-ball tournament for the long weekend. On Saturday morning I woke up and it was hot and humid. I drew a bath and shaved my area into a tight landing strip. Then I put on jean shorts, a tight polo crop top, and black leather ankle boots. I knew Juan would be at the park around 2 so I made my way there and stood on the sideline.

He dominated on the soccer pitch as usual, scoring two goals. Watching his tall, tight, shirtless, pierced and tatted body in action made my knees weak and my pussy wet. When the game was finished he came over and greeted me with a kiss on the cheek. We discussed going out for drinks but he said he had to go home and “change first.”

Less than half an hour later we were at his place, a beautiful airy loft. I perched myself on one of the stools adjacent to his kitchen counter, waiting for his move. After emerging from the bathroom he wasted no time, kissing me. I pulled his shirt up over his head and off, and rubbed my hands all over his lean abs and chest. Using one hand to reach up my tight top and gently pinch my nipple, he used his other hand to undo my belt. With me still sitting on the stool, he lifted my legs up and pulled my shorts and panties off. As soon as his fingers penetrated me I squealed with delight. The bulge in his shorts was massive now, and when I pulled them down, his cock bounced out and slapped off his belly button. It was long, thick, and uncut. My hand barely grasped its circumference, and I licked my other hand and started to stroke him off.

“I’m gonna fuck you right here and now,” he said, taking control and lifting my legs up.

With my back against the counter and still perched on the stool, Juan entered me. I had never felt a cock so big, and it took a few moments for him to build his cadence. But once he did, I was in pure ecstasy. Completely filling me with each thrust, he worked his way from slow, languid strokes to hard, jackhammer fucking. I was moaning and screaming as he used one hand to work my clit and another to steady me on the stool. His height was perfect for this, and I started coming over and over again.My juices squirted out onto the stool cushion with each recoil of his giant cock.

When his groans started building, I knew he was close to coming. I bucked up hard into him, and with some final thrusts he pulled out of me. There was an audible pop as I came hard again, and my entire body started shaking. A long rope of come shot out of his cock and all over my shirt. I grabbed the head and started kneading it as he kept ejaculating. I absentmindedly began rubbing his hot essence all over my stomach as he shouted out “Fuck!” three times in rapid succession.

My whole body felt the orgasm, and I tingled all over. He started laughing and engaged me in a deep kiss. Our months of flirting and sexual tension had culminated in this quick, five-minute fuck, and I was exhilarated.

We gathered ourselves and tried to decide what to do next, but my black top had his semen all over it. Laughing at the situation he offered to put it in his washing machine. I borrowed one of his soccer jerseys to wear while it washed, and sat on the couch and smoked a joint. It wasn’t long before we were going at it again.

In all, we fucked four times that day.

Moms Secret

I was 15 when I caught my mother cheating on my dad. School ended early that day and when I arrived home mom was nowhere to be found. I went upstairs to my room, but as I passed my parents' bedroom I could hear a groan. I looked through the keyhole and saw my mother, naked on her bed on all fours. There were two other people there. One behind my mother, the other in front of her and both penetrating her.
I watched for a moment and couldn't believe what I was seeing. The two others were boys from the neighborhood. One 17, the other 19 years old. I could see them taking my mom hard and she was enjoying it. They slapped her butt, called her bitch and both finally came inside her.
I never told her that I saw them. Nor did I ever tell her that I jerked off right at the door.