Daddycool

Daddycool Avatar
Gender: Straight Male
Age: 35
Relationship Status : Not specified
Profile Visits : 274
Number of Comments : 7
Number of Confessions : 0

Daddycool's Favorite Confessions:

Trying Something New

I am a normal, everyday, suburban, white, divorced mother of three children. My parents live in the same neighborhood and always help out with my kids. My ex husband is a great dad as well a good support mechanism for me.

Over the last 30 years, I have gone from a young girl trying to understand her young body to a woman who knows exactly what her body wants and needs.

About two years ago, I ‘matched’ someone online. The messaging went like wildfire and I found myself in a quandary - Darren was a black man. I am a progressive and open minded woman, but suburban America isn’t ready for this, nor would my parents be. I explained this to Darren and he was understanding. When we chose to go out for dinner, we made sure we stayed clear of either of our towns. This date ended up as a one nighter that ended up with each of us getting each other off in his car.

I dated other guys, white and black, but I found I desired the black men more. I think it was the societally ‘unacceptable’ of it all.

Anyways, then along comes Brian. Brian is a polished, respectful, well groomed, father of three girls. He is an attorney and has all of his life together. We go out and he asks if I am interested in spending more of the night together. I said I would enjoy that (if he only knew the dampness making my thong stick to my pussy). He asked if getting a hotel room would be acceptable and I agreed. We found one, checked in and found the room. I texted a friend telling her where I was and I texted my mom thank you for having the kids tonight. I was a free girl tonight…

As we get into the room, Brian closes the door, leaving he and I standing in the dark. I feel him behind me and I get nervous….until he says I am going to kiss your neck. He moves my hair, kisses my neck, grabs my hips, pushes me against the wall. He then says may I unzip your dress? At this point, that man could have done anything and I would have agreed to it. I answered yes and within seconds I was pressed against the wall only wearing a thong. My nipples were rock hard. As they dragged along the cool wall, flutters of energy found my hot pussy.

Brian spun me around and his mouth found my nipples. God, I was so turned on. I reached for his belt, making him stop tormenting my pink nipples. He stepped back, allowing me access. May I take off your pants? He answered me with feel free! We are both bare chested and barely covering our most intimate parts. His obviously hard cock is straight out from his body, covered by maroon and silky boxers. I reached in and pulled out the perfect cock. 9”, thicker than my hand could wrap around, thick bulbous head and a sack that hung. As I stroked him, he found my engorged pussy and began to stroke her. We are still in the dark….and we started kissing. I am soaked and he is rock hard.

He reaches down, grabs my legs and he mount my pussy on his cock. No condom, no hesitation, no asking…he just did it without even stopping kissing me. My pussy lips convulsed as he lowered me in his hung cock. He strength and his power…good lord….he had me folded in half, with my feet up by his head. He pressed my back to the wall and started to fuck me. Although I felt save in his embrace, the position was new for me and I wasn’t sure about it…but he had control. He obliterated my pussy as he bounced my white body like a rag doll. I wrapped my arms around his neck and let it happen. I came and he never stopped. He slowed to ensure I was good and continued confidently. Multiple orgasms later for me, in the bed in the missionary position, we says I will have to cum soon. I responded with an okay. As he started to fuck me again, I looked into his eyes and said ‘you can cum inside of me or on me, I am good with both.’ He picked up the pace, his body tightened and he flooded my well fucked pussy with his cum. After a few more minutes of fucking, he pulls out. I grab is cock and pull him towards my mouth - yes, I wanted to taste his cum.

Brian has been my ‘shadow’ boyfriend since!

Working Hard

My neighbors have always been very nice and friendly. I work from home as an IT guy Covid made my position a work from home job. I purchased a home in 2020 during Covid. A bigger house home office pool something mice’s then what I had. My neighbors super nice one side of me was a retired RN who travels a lot and is rarely home. To my other side is John and Jenny. John is a long haul driver who is gone 3 weeks out of the month and is rarely home. Super nice guy who introduced himself one evening when I was in the garage. We talked over a couple of beers which was nice. He introduced me to his wife and 2 kids. His oldest was getting ready to leave for college and the youngest was a junior in high school. Both very athletic both had nice asses. Soccer is what they care into form what he said.
Then in comes Jenny. Jenny was a thick woman taller about 5 foot 7 maybe 140-150 lbs. She has dark brown shoulder length hair a pair of leggings that showed off her ass good and some thick camel toe as well as a snug shirt that showed she had some big tits as well. She wasn’t a heavy girl just thick and curvy. She introduced herself to me I offered her a beer she accepted and i talked for a while to both of them. There eldest called there dad as she couldn’t find something in there garage. He excused himself and left Jenny and i talking. I explained I worked from home she told me that since both girls drove know her days where easier then before. She had thirds lips that I was amazed with. All I could think about was how it would feel to mouth pump her. I came back to reality when she said it was going to be nice to have someone to talk to. I gave her an open invitation to come and talk when ever she wanted.
2 days later around 9 in the morning I heard a knock on the door. It was Jenny saying that she was alone in the house as the kids were gone and John was headed to the east coast.
I was busy but I was not going to pass a chance up to see how far I could go with Jenny. She did this every day with each day a little more flirting and more sexual tension. From the first day she came over early and leave right before her youngest would get home. Most days her youngest would be home then leave for practice or tutoring and be gone until later in the evening. Again Jenny would come over as soon as she was alone. After about a week and us getting touchy feely with each other I told her tomorrow to come over in a swimsuit and we will go swimming. I said it in a way I was telling her to not asking her. Next morning she came over and had a wrap on. She walked in gave me a hug as we hugged I manned up and gave her ass a squeeze. When i did she let out a soft moan. She looked at me and i took her wrap off. She said that she was a bit nervous specially in her bikini. It was a small 2 piece and her nipples where big and the top was barely keeping the in. Her bottoms rode up high and disappeared between her ass cheeks. There was no stopping us now I had her bent over the table and was licking her rear and pussy. We fucked for most of the day. When her youngest came home she text her to let her know she was out with friends and would see her later that night. That was almost 2 years ago and I have been treating Jenny as my own wife. Her youngest daughter is now away at school as well. John comes home for about a week or less. When he leaves Jenny comes over or il spend the night there. Jenny has learned to take and like anal. John has talked to her about possibly moving but Jenny put a stop to that telling him she liked the neighborhood and felt safe. He calls her almost every night and most of the time she has a mouthful of cock or I’m buried in a hole and have to stop so she can talk. Sometimes I give her really slow strokes and it drives her nuts. I have hours of us fucking and tons of pictures. I have a really good picture I took of her. We had gone out for dinner one night. She got dressed up make hair tight dress looked hot. Bright red lipstick on those lips. She is on her knees with my cock about half down her throat. Her big red lips are wrapped around my cock. I took a video and pictures of it. The pic of her lips wrapped around my cock is what comes up when she calls or text me. I also have it as my screen saver. She has a kink side to her as well. During the cold weather she took outside got ok all 4s and started to dildo herself. She wanted me to see how much steam came from her pussy. I took pictures and videos as well. She really is what you would want from a woman. Cleans me up afterwards and doesn’t care what hole I was working.

My Ex Spouse Ruined Me

I was with my ex wife Shelbi for 4 years, married for a little less than 3 of them. I truly hated everything about her from early on, but caved to pressure from family and friends and stayed with her for far too long. Before we were even married I had a hard time fucking her. She wasn't ugly, I just wasnt at all into her as a person. I'd have to watch porn as a primer and put her face down to bust a nut. Shortly after we got married we came to a mutual understanding that we did not want to fuck each other, or even sleep in the same room.
Initially this led to us having an open relationship. Which quickly turned into swinging and wife swapping. Once this slut was turned loose at a party she'd let every last guy run through her, which honestly worked out for me, as I'd get to fuck many of the wives of the guys fucking her. I vividly recall standing in the kitchen of a little apartment getting a bj from one of the guys wives and then fucking another while Shelbi was in the living room having a train ran her with at least 10 men taking turns on all of her holes. I finally divorced her after she caught a serious std. Not that I had any risk of getting it from her, but it was a solid excuse to finally ditch her.
The bad part about having lived this lifestyle, I now find it very difficult to get off from "normal" sex. Even though it's been a few years since I left her and that life behind, normal sex seems boring still. It has led to me trying to spice things up with my previous girlfriends and current wife. It usually takes exhibitionism or fetishy sex to really get me excited. Luckily my current wife is ok with being seen by or fucking in the presence of others, but for how long she will entertain my fetishes I just don't know. It really is out of her comfort zone though, and she lets me know. This is a woman I am happy to live my life with, and know I need to change, but it's like an addiction. I truly wish I'd never got with my ex wife and experienced the things I did with her, because prior to being with her I thoroughly enjoyed good old fashioned sex.

Problem With Beautiful Girlfriend

I have a big time problem with my girlfriend. She is 21, very very petite, with just barely there puffy areolae and nips, no tit growth at all. She is totally beautiful with long, soft brown hair. She is thin, petite and keeps in great shape. So, what's the problem right? She honestly looks like she's 12 years old. Even at the beach, or anywhere. People stare at me like I'm a perv dating a girl instead of a woman.

My friends were the same, and their girlfriends were terrible about it, till they found out she's old enough to drink and has a real ID. She graduated college and to be honest has appeared in some porn for those who like the young stuff. We've been going out now for about a year, and she is incredible. She is wild in bed and can't get enough. She cums super easy, and let me pop her in her pooper too. She will wet herself, go in public and exhibit herself, fuck in public, be a sex slave for a weekend, and loves an over the knee spanking with hand, belt or paddle, you get the idea. She is perfectly suited for me, but even with me sometimes I'm fucking her and look down, pinch those barely there nipples and see this little girl looking up at me.

WOW, helluva dilemma. Love her, don't want to stop having sex with this dynamo, but everyone thinks I'm perving on some 12 year old or something.

Bad Decision, Now An Obsession

This story goes back 12 years. In todays high school world it is popular to be "trans or non binary". A few years back it was popular to be bisexual (I know from my niece). Well back 12 years ago in order to be popular or one of the cool girls you had to date or fuck black guys. In my parents house bringing home a black guy was not an option. But I wanted to be one of the cool girls. Didn't quite work out that way. I was 16 and dumb.
There was a stairwell in the back of the high school where all the really hard core black guys hung out, skipped class and smoked weed. Please don't take offense at my french here. These guys were "n*****s". Dressed the hip hop, thug part. One day I got up the nerve and went into the stairwell. I was immediately confronted by 2 boys. I was so nervous I decided to just walk by and head upstairs. One of them grabbed me by the arm and started feeling me up. He pulled me under the stairwell out of site and told the other boy to keep watch. He pushed me up against the wall and groped my tits as he kissed me. I tried to push him away be he wouldn't stop. He got the front of my jeans open and pushed me to the floor. I was on my hands and knees as he pulled my jeans down to expose my ass. As I felt his cock start pushing inside me I could tell it was much larger than the white boys I had been with. During this he kept yelling things back to the boy keeping watch. Things like how tight my white pussy was, how he was stretching my white pussy, how he was training this white bitch. I cried a little and felt ashamed. I was being used like a piece of meat. I began begging him not to cum inside me. He told me to "shut up bitch". When he came he yelled "this bitch is having a black baby". After he got up and walked off like nothing happened. I pulled up my jeans and spent the rest of the day with cum leaking out of me.
And yes, a few weeks later I missed my period. I wasn't one of the cool kids. My parents were less than happy I was pregnant, but went meltdown after i told them the baby was black. Went to a clinic and made it go away. We moved shortly after that.
Problem is no matter where we lived I kept fucking this exact type of guy over and over. Only difference was I was now on birth control. My relationship with my parents was crap. I left home after graduation.
I never married or even had a real long term boyfriend. Nice guys don't exactly like the fact I have this habit of fucking this type of men. But it meets my sexual needs.

Home Sweet Home

Home Sweet Home

I’m a business man 37 years of age. I have a larger home, 4,500 square feet. I hired a young woman, Abby, a neighbour’s daughter, an attractive twenty-two year old, to clean my home once a week. I’ve watched her grow up from a spindly young woman to what she is today, an attractive full figured one. Her mother told me that Abby started her own home cleaning business and asked if I could use her services adding, “It would really help her out.”
I’m away with work, sometimes as much as a month at a time so being that is the case and that it would help her out, I took her offer up. I have security cams all around my home indoors and out. The cams alert me to movement and such and she herself sends me a texted “thumbs up” when she’s finished. She’s been cleaning my home for the last 10 months with me having no complaints. Recently however, my bedroom cam caught her masturbating on my bed. Don’t get me wrong … a beautiful sight but, my bed. I could tell that she knew where the camera was located because she was playing up to it. It got me thinking, normally I never check the notifications because I know her schedule and well, who thinks that someone is doing anything other than their job? So I checked the other cams and found that yes, she has been masturbating in every room of the house and doing most of her work in the nude taking full advantage of my pool, hot tub and sauna. I have to admit I found it humorous that there I was away from home masturbating to all these vids of her in my home, masturbating. Again a beautiful sight but why? I made no mention of what I had seen this whole time. She gets very creative with her use of bananas, cucumbers or my favourite, her fingers but her last vid she left her panties on using a vibrator outside her panties to get herself off giving them a good soaking. I never have any communication with her when I’m home and other than her thumbs up text messages while gone, that’s it. On this my last home visit, as I laid in bed, I felt something under the pillow. It was a zip lock bag with that very pair of soaked panties in it and a note saying, “These are fresh off my wet vajayjay. I’m available anytime. Just text me! Abby”
Well, after sniffing her panties there wasn’t need to convince me further so I did. She was over within the hour and believe me, she rocked my world.
She came over like she owned the place in a short, short skirt, no panties and a totally see-thru top. She planted a deep kiss on my lips, walked over to my marble top bar, laid down on it spread eagle and simply said “pull up a chair and eat me.” Which I did. Quite the night.
More to cum.

Needs The Job

I currently work for my dad who owns a large manufacturing company in a small town in the west coast. His shipping department is where I have been working. One of his good friends is head of shipping and he has an assistant named Anita. She is in her mid to late 30s long dark hair small tits some big hips and a very large ass. I used to call in to work alot until I was moved here and worked with Anita. She is usually in jeans and they fit tight around her ass. We shipping all went out one Friday after work for drinks. We all had a few and I got to talk to her outside of work. Found out she was married 1 kid and her husband is a dead beat who can’t hold a job. She said that she had to go because she couldn’t spend to much on drinks since money was tight. I offers to pick up the tab because I told her i enjoyed talking our side of work. She agreed and I agreed to also take her home. We had a few more drinks then decided to head out. I gave her a ride home and get a few drinks we got a little touchy feely. I ended up kissing her and got to feel on her ass a bit.
This went on for a few more Fridays. She said she had to stop because she was having mixed feelings about her situation. While at work I started to slowly rub on her ass or would make some comments when we were alone. Nothing mean and after she gave me a little smirk when i was rubbing on her ass I continued it.
The following Friday she hopped in my truck to head over to our watering hole and she says that she has been letting me get away with all this ass grab and comments because of who my dad was.
I never once forced her to do or say anything. She saw that I was a little upset and she apologized for thinking that way. She said that she needed this job and did not want to risk loosing it. By that time we were in the parking lot talking. I reached over gave her a kiss and pushed her head onto my lap and told her to suck my dick. She hesitated for a minute I had pulled my dick out and then I could feel her breath on my dick head. She sucked me off and after a bit she was really into it. I shot my load and we went into the bar had some drinks we talked as if nothing happened. When I was ready to leave I tapped her shoulder and said let’s go. She picked her stuff up and and we headed out. When we got to the truck we had a heavy make out session and I took her pants off and I got her to ride me. She felt really tight and as she rode me I slid my finger in and out of her butt. She asked me not to cum in her and I went ahead and shot my load in her. When we were done she got dressed I drove with my pants unbuttoned and had her blow me in her driveway one more time.
I told her that I would come by and pick her up tomorrow. I would text her what time we were going out. She cleaned up wiping the spit and cum from her lips and face and went into the house. I text her the next morning letting her know I would pick her up around 4. Centers me a thumbs up. I pulled up and she came out in a hot little skirt and a matching top with some boots. I asked her what she told her husband and she said that he was at his moms with there son and would be there until Sunday night. We went to dinner and I fingered her in the restaurant had some drinks and brought her back to my place. We spent the rest of the evening fucking letting me have access to all of her holes. I took her home the next afternoon and we went into her bedroom and I did her there a few times as well as doing her ass in the living room.
This has been happening for a few months now and she has enjoyed every moment of it. She said that she never thought she would enjoy being a sub. I have started to fuck her artwork as well. We have some down time during the day when our boss goes to lunch with my dad. So we take a little longer lunch and eat then fuck our brains out. She made the comment to me saying that she loves me and I said it back because I was horny and wanted to spend some time in her ass. Every time I slid it in her butt I would tell her how much I loved her.

Great Times Showing Me

When i turned 18 my mom had a really good friend that happened to be a neighbor around the corner. She was a fit dirty blond, was about foot tall right bubble butt and a pair of tits that you could not believe where on a body that size. She had a son my age but he was never around. He ended up in trouble with the law all the time and would always argue and fight with her so he picked up and moved on with his dad. The ex husband was a real piece of work. Owen show own business but would go out all the time come home drunk or not come home at all. My mom asked me a few times if I could go to her house and help her move some furniture around and help her with the yard work.

I had a huge crush on her so I jumped at the chance to be alone with her. I showed up on a Saturday morning knocked on the door and she answered it and I was flabbergasted. She was in a small white tank top that was fitted. Her tits where clearly visibly popping out and she had a tight pair of shorts that the material was very thin and where clingy. As she moved around you could clearly see she had on no underwear because of the massive camel toe that was showing. I helped her re arrange her furniture move some boxes in her garage. When on the garage she was on a ladder looking for a particular tub in the rafters and asked me to get close so I could get it from her. I was at base of the ladder making my face about 2 inches from her butt. I put my nose as close as I could to her crack and took a whiff. I was so close I could feel the heat coming from her rear and she smelled amazing.

I wasn’t paying attention and the tub was a little heavy and as she grabed it off the rafters she lost her balance fell back shoved her ass in my face and dropped the tub. The tub fell to the side hit my shoulder and I had my face buried in her butt. I pushed her up and I was very red in the face. She climbed down checked on me to make sure I was ok which I was she then went over bent over and checked on the tub. She bent over right in front of me and her shorts were right up her booty. I don’t know why but as she was bent over in front of me I was rock hard at the time I gently reached down slid my fingers under her shorts and pulled them out of her ass for her. She didn’t say anything she just looked at me and I told her that i just wanted to help her with her shorts. She didn’t say anything so I went to the restroom and arranged my dick that was now rock hard. I came back out and she was bent over looking into the tub. She was getting out what she needed and as walked up she asked if I could put the tub back. I picked it up climbed the ladder and put the tub back. When I got back down she thanked me and I said no problem giving her a little smack on her butt. It did not faze her so a few minutes later I asked her if she could get me a glass of water as she walked away I gave her another smack on the ass. She waked away went into the kitchen and came back about with a glass of ice water. I took it from her thanked her and took a drink. She stood there talked a bit. She was standing next to me and as we spoke I asked her if she was tired and she said she was she then leaned her head on my arm right below my shoulder and I put my hand right on her ass cheek. I would swirl my fingers around it. There was no doubt about I was now rubbing her ass almost as I was giving her a massage. Now she is a single mother. Things quickly escalated and we ended up fucking in the garage the living room and bathroom and bedroom. She was in her late 30s I barely 18. I use her holes for my personal pleasures. She was the first women to let me in her butt.

I could grab her by the waist and almost have my hands touch. I am now 26 she in her mid 40s. Her ex husband and son are no where to be seen. She still looks amazing, she looks like she is in her early 30s. My mom was a bit upset when I moved in my dad understood. It’s a great feeling to see her walk into a restaurant or bar and I watch all the people around her turn and look. Women give her dirty looks men check her out and I get to fuck every hole.

She has a kinky side to her as well. She sometimes wants me to fuck her in the car before we go to dinner. Then she gives me a play by play of how she can feel the cum leak and run down her thighs. I sometimes feel down around between her legs and slide a finger in and can feel the sticky mess and she then cleans my fingers up. We usually cut dinner short to fuck when she does this. Under the table bj if it’s private enough. Pretty sure our waiter knew what was going on last time we did this. He kept trying to look underneath with out being obvious . I moved myself in about a year ago. We both have a high sex drive so it works for both of us.

Is This Cheating?

I have a confession, and I could use some advice.

My (19M) girlfriend (18F) and I have been dating since 9th grade. I graduate next year, but I'm staying in Dallas for college, so we're def staying together. We have a great relationship. Shes a sexy brunette with cute little tits and a juicy ass, and shes super affectionate and loving. I've never even considered cheating on her.

I'm pretty close with her family. Her mom is a very beautiful woman from Colombia, who works at a hair salon, and her dad is a contractor construction guy who moved to Texas from the east coast somewhere. Theyve always been really nice to me. She also has two sisters, one younger (like, eight or something) and the other a few years older (21 I think).

Heres the thing. My gf's older sister is super fucking hot. She has really big tits, totally not like my gf, and a tiny waist and round, bubble-butt. Her family has a pool, and sometimes we'll all be swimming and my gfs older sister will come out in a bikini and I always have to hide the biggest boner because honestly shes just so fucking hot. Shes funny and nice to me, but we're not really that close, and I (beyond many times jerking off to her) never imagined anything more than that really happening. And, nothing ever has happened.

But last week I found my gf's older sister's OF account. I dont think anyone in the family knows about it, I obviously didnt say anything to my gf. She is super cool about porn and stuff like that, sometimes we even watch stuff together, and she doesnt think its cheating or anything when I watch porn alone. But obviously her sister would be different, right? Theres some free stuff on her sister's OF page, and I couldn't help it, I had to look at it. Its pretty tame, mostly just kinda dancing around in a bra, but I still shot buckets to it. And I can't stop thinking about subscribing. She would never know it was me, and I can tell some of the pics and videos are full nudes, and even some look like shes fucking a guy. I can't get it out of my head, I want to see her naked so bad, but I feel super guilty because I know her sister (my gf) would definitly not be cool with that.

Has anyone ever had a situtation like this? Is it cheating to sub to my gf's sisters OF? It feels different because its someone I know... and her sister... but I want so fucking badly to see what she's got under that bikini.

My Young Friend Sells His Wife To Me

I'm a middle aged guy who has never had a girlfriend. I was able to earn a lot of money but never learned how to be attractive to women. I spent my days watching porn instead. A few months ago, I made friends with a younger guy who was married. His wife is gorgeous. Like a model. Both are pretty young, like in their late twenties. The guy is the fuckboy type but he never got a job. He told me that his wife always complains about his unemployment because she came from a rich family. They seemed to be fighting almost everyday. I offered him a referral at my workplace but he doesn't want to work. He is the lazy kind. One night we were drinking together and I got a bit drunk and suggested him to let me fuck his wife if I give him money. I offered him like 50K per night. He knew I had the money. He went silent and stared at me with a deadpan face. I got a bit scared. Then he said that will shut that bitch up. I didn't realise he was drunk too. I didn't open my mouth after that. The next day I didn't mention anything about it but he brought it up again. He actually agreed. I couldn't believe it. He invited me for dinner one night and I brought a cheque with me. I was so excited and horny to fuck her. I never even talked to her other than simple greetings and I knew she found me unattractive and probably even disgusting. The whole night I made comments about how sexy she is and she was visibly uncomfortable. After dinner, the guy said he had to go somewhere and left me alone with his wife. She looked puzzled and annoyed at him. After he was gone. I explained everything to her that her husband sold her body to me. She looked furious and was about to cry. She was alone with me and at my mercy. I slowly undressed her and saw her beautiful tits. She started to sob when I sucked her nipples. I fingered and licked her pussy and licked every inch of her body. Then I pounded into her without mercy. She sounded like she was both moaning and crying at the same time. I grabbed her hair and came on her face. Fucked her as good as I could. Then I signed the cheque and placed it on her tits as she lay on the bed. When I went outside the house, the husband was just outside, smoking, probably listened to the whole thing. Sick motherfucker. As I started to leave she called at me. I turned around and she was there, still naked but covered in a bedsheet or something and my cum still on her face. Then she did the sexiest thing ever. She tore the cheque right there and said I could come to her any time I wanted and FOR FREE. My dick got hard and I had to stop myself from going another round. Then she looked at her husband who looked shocked, and said that he would have to pay if he wanted to fuck. Then she went inside. The guy looked at me and I couldn't help but smirk at him before I left. I've gone to their house almost every day for a week now and every time her pussy feels like heaven.