Daddycool

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

Daddycool's Favorite Confessions:

Horrible

I hired an assistant that I really didn’t need. Mostly as a favor for an old buddy. Same age as me late 40s. Wife has empty nest syndrome as there only child left for school. I own a large mfg company married young had kids divorced and then primarily concentrated on providing for my 2 boys. There mom and I get long differences between us just made things difficult. My old buddy whom I rarely see anymore ran into me at our golf club. We sit at the bar and goes on and on. This guy is not a saint by any means. He is probably pist because now that there son left his wife wants to spend time with him and he wants to fuck around like he is used to. He pretty much wants to find her a part time job to keep her busy. I remember her being a thick brunette always looked good. I agree to meet with her and I honestly decided to hire her the minute she showed up at the bar we were at. She was in a blouse and short skirt. Her tits were massive. Must have gotten them done her lips where plump and her short skirt hugged her ass. She was very nice and we hit it off. He went to the range while I interviewed his wife. She wasn’t the smartest ever I told her that we would be spending a lot of time together and she would be my personal assistant. May require long hours. She perked up and said that it sounded important and she would love to give it a try. First day she showed up dressed to kill. Her tits where showing short skirt. Every time she leaned over her nipple would almost pop out. I put her in a spot where I could see up her skirt when she sat down and in plain view of her tits. Her name was Erica. She had these natural big full lips. After a week I had just come in from a meeting and I walked in before lunch and she had lunch there for me. Wow she surprised me she knew what my favorite sandwich was from the deli i usually went to. We talked and she told me she was happy to be here. I told her that she was doing a great job. A few weeks went by and same thing lunch ready coffee in the morning. Snack a little after 3. One evening she is getting ready to leave and she is getting her things and she says oh here is some more bottled water and a protein bar I know you will be working late and comes over to place the bar on desk. I was standing up when she placed the bar she got close and gave me a kiss. I gave her one back and rubbed on her ass a bit. This went on for another week when one evening I asked her to dinner. She accepted and would stick around and wait for me. Again she gave me a kiss but this time I kept her in front of me and started to undress her. On my desk she sat legs in the air blocked her rosebud and her pussy licking thighs. Almost full dressed she mounted me on my chair. Her tits where out of her blouse and she rode me as we both came to an orgasm. I took her to dinner fucked her again afterwards. I have been fucking her freely since then with some really good blow jobs. I ran into her husband after a round of golf. He thanked me and said that she was off his back and from what she told him she was really enjoying what she was doing. I thought to my self of course she is she is getting fucked just about every day. Erica an I did an experiment to see what his reaction was. I took her to my house after work and we fucked and stayed late. I mean it was almost 2 in the morning when she left. The next day she said her husband got up and did not say a word. Friday came and cairn she comes over after work. We go to dinner come over to my home and this time I kept her over. We fell asleep in my bed she woke up around 7:30 when her phone went off. She wakes me and shows me her text from her husband. Her babe saw you went to the gym early today. Went to the club will be back super late. Some buddies and I way head on a road trip for a few days would that be okay. She had my dick in he her mouth as she was texting him back. Oh that sounds like fun. I’m going to hangout by the pool and maybe get a massage. Have fun be careful. I driver her to her house she had me fuck her on there bed. Grabbed some clothes and spent the next 5 days with me. She went home the day he was supposed to be back. He text her that he would be extending his stay a few more days. She again showed me the message. No problem I’m busy at work. I think it’s over between them and I asked her to move in with me. She laughed and said I don’t have to tell him anything. Il just show up at the house on random days. This has been going on for about 6 months and he thinks that she is ok. I run into him at the club and he bought my guys a round of drinks. He was tipsy and let it out that he has had a really good time since his wife went to work for me. I told him no problem I can keep her really busy over the weekend with out of town projects if that’s ok. His face lit up. I told him I had a week long trip coming up and would take her with my group. I surprised Erica with a trip to Cabo

Two Sisters Couldn't Be More Different

In Las Vegas for a bridesmaids party I was unceremoniously fucked and married one night to a man I met there. Dragged away from college, put up in a house in New Mexico, I adapted to a man whose idea and life were for an old fashioned woman. Over the following year I had a child.

The man I married owns several businesses and I work beside him. Literally his son at his knee. In time a daughter joined us, she is now four and her Daddy wrapped around her finger.

My sister, with so much ceremony married and divorced two years later and is both an alcoholic, IMO, and a fair weather lesbian.

Lifelong Dick Sucker

It is silly that I feel compelled to admit this, but here goes. I am 60 years old and I have been sucking dick since I was 15. My first taste was my brother’s best friend. Over the years, the number of dicks I have sucked is basically uncountable - but I have to be over 1000 dicks so far. I have sucked literally every variation of dick. I have sucked friends, boyfriends, bosses, my dad’s friends, etc. I am a swallower even at 60. Thank you for listening to my confession:)

Sorry Bro

As the title says I couldn’t help and keep my dick in my pants on Saturday evening and into Sunday morning. My neighbor Robert had a niner watch party on Saturday. About 15-20 people there lots of booze pizza to make it easy. I have always had a thing for his wife Christine. She is olive skinned has shoulder length dark hair usually in a pony tail glasses had massive tits a small waste and these giant hips and and ass the stock out. Kind of looks like a hispanic Jessica rabbit. She and Robert argue a lot and in front of people. She is actually really mean lol. Anyways we were all having a good time Christine had on a niner jersey and it was long and it actually looked as if she was not wearing anything under it. I was bold and had some courage as we where outside when I asked her flat out if she was going commando. She laughed and said yeah I’ve got nothing under this and lifted her jersey to show me she was wearing these fitted running shorts. I made another crude comment saying damn that ass legit. She laughed and asked if i liked it. She then proceeded to bounce is up and down causing it to really jiggle. She was so into it that she didn’t notice that I had my phone out taking some videos and some pictures. I then put my phone down and started to smack her cheeks. She got closer for me to smack that ass. She stopped for a second to make sure no one was around. She then said stay here. She went into the house came back a few minutes later and said follow me. She had a drink in hand and had a little trouble walking. The other side of the yard
Was another wall and there was a part that was secluded from the rest of the yard and there bedroom was there. On the other side of the fence was my house. I asked her if she brought me over here to shake that ass for me again. She said that she did. She lifted up her jersey and and had taken her shirts off while inside and was wearing a bright red g string. She said don’t tell anyone but I like to dance and I will only dance for you. She said I couldn’t touch and she proceeded to dance for me. I had my hands on her ass cheeks a short time later. Her skin was really smooth and soft. She gulped down her drink struggling to stand with her jersey lifted I pulled my dick out and as she was looking to sit I sat her on my lap. Since she was only wearing a g string I was able to pull the material to the side fairly easily and slid my cock into her. She didn’t say anything and had her eyes closed. She then proceeded to move her hips back and forth as I had bottomed out in her. I told her how tight she felt she said you’re not going to tell anyone right. I told her of course not and then she started to ride me. She looked amazing I played with her asshole while she jumped away. I took my phone out and recorded the whole thing in case this shit went south. She tensed up and made some noises and let out a moan when she came never stopping her rhythm. I by this time had pulled her jersey off and was playing with her titties and nipples when I chit a load deep down inside her walls. She sat on me for a few while I sucked on her tits. She looked at me and said we should have used a condom. I gave her a kiss and she said that she needed to Check in on the party. She couldn’t find her panties I had taken them slipped her jersey back on told em to meet her out here again in 30. I hoped my fence and went back to the party from the front yard. Christine went in from her bedroom. I talked to her when I was back inside. She asked me if I was ready for round 2. By this time most people where so fucked up we could have fucked there in the living room and no one would have noticed. No one was really paying attention or was the end of the game people where leaving I stayed behind to help. We had fucked 2 times already and I was not going to leave with out putting my cock right up her butt. That was all that was left for me. She was still in her jersey and no panties. She had a few more drinks and then came over to me and kissed me. I sat her down outside and went in to see Robert. He was dead asleep on the recliner. I took Christine around so we could see the back of his head and I put her on all 4s so we both could see The top of Robert’s head. I put my dick right to her little puckered up ass and proceeded to push it in. Surprisingly it went in easy. She was relaxed because of the alcohol. She said something about she doesn’t do this. Not sure if she meant cheating or anal sex. Either was I had my way with her and finally after some rough hair pulling and rough anal I shot a load in her. I shot a video and took some photos of what it looked like. The next morning I got a text of we could talk. I met her in the backyard she said Robert was till asleep and said that her ass was sore but she had fun. She came over in the afternoon and this time we did everything again just sober. Looks like I have some pussy on command for now.

The Freedom Of Being A Stranger

I’ve known for a long time that I am aroused by being naughty in places that I shouldn’t. It started in high school when I masturbated in field. No one was around but it was so liberating and exciting to feel the sun and wind on the parts of my body that we keep tucked away. In college I would go to the library wearing just a skirt and an oversized sweater. At any moment I could easily access my pussy or grope my breasts. Just the feeling of being in public with my nipples freely rubbing on a soft bit of knit fabric made me ready to cum.

I’ve been afraid to explore this kink now. Living in a small town were everyone knows me, it’s too risky running into someone I know. But I would think about how fun it was in the past.

So this past week I’ve been in a city for a conference. It’s been a relief to get away and I like the feeling of being anonymous in this place that doesn’t know me. Last night after a dinner with colleagues I went back to my hotel a little buzzed. I get horny in hotels and was naked, enjoying touching myself. I thought I could use a little wine and had a really naughty thought.

Instead of getting fully dressed I just put on my long winter coat. I went into the hallway and the fear almost forced me back into my room. I took a deep breath and decided to commit. In the elevator I was so nervous and my heart was racing. I was totally naked under the coat. I convinced myself that no one would know and stepped out into the world. My skin felt so soft against the inside of the coat and my arousal was overwhelming.

The store was about a block away. I took my wallet out of my coat pocket and slipped it into the interior pocket, knowing full well I would have to open the coat to make a purchase. I grabbed a bottle of white wine and went to the counter. The cashier told me the total. With a rush of blood I untied the sash of the coat and opened it to reach for my money, exposing the fact I was at least topless underneath. He looked surprised but was polite. My heart was pounding as my naked breasts hung in front of him, partially obscured by the coat. When he gave me the card back I opened it further to put the wallet back, and with a smile fully revealed my naked body and hairy pussy. I said thank you and made off into the night.

What a rush. I had to sit on a nearby bench in a quiet park and make myself cum. That’s when the embarrassment set in but I have no regrets. What can I try tonight?

Wow, What An Amazing Experience

I was on a business trip about a month ago. The day finished and Jane and I decided to just go to dinner in the hotel bar. Simple, easy, no fuss.

Well, four drinks later and we start talking about sex. It was silly, funny, awkward, naughty, but it led to an amazing experience.

We had figured out that both of us wanted to play with another woman. So, we both decided that night was the perfect night. We bought a bottle of wine and headed to my room.

Hooking up with a woman: not in my wheel house nor in Jane’s either. As we fumbled our way through this, we both started laughing so hard that we knocked over a glass of wine. We both got on the floor to clean it up and the night began….eye to eye…we just kissed each other.

Piece by piece, kiss by kiss, our clothes came off. Jane was a beautiful white girl, me being a beautiful Latina. It felt so right, so we ended up in the bed. Kissing, touching, sucking, licking…then some fingering. She made my pussy cum so good. I returned the favor in delight.

We spent the next two evenings in each other’s bed. After the business trip, we went back to our regular lives. Maybe one day I will do this again.

It’s Ok They Don’t Know Your Name

I took our office Notary out to lunch. I have asked her a few times and she finally agreed. She obviously knew that the times before I was hitting on her. She is a short brunette has nice tits a tight little ass that she tends to show off as she wears stretch pants. What really get me going is her lips. She has these really big puffy lips. I tend to flirt with her when she drinks from her water bottle or form her bottled soda. She is engaged but I do t really care. I asked her to lunch and agree to drive. She accepted and it was quite pleasant. She enjoyed it and confessed that she was nervous that I would try and make a move on her. Fast forward to last Friday and again I asked her to lunch and she quickly agreed to it. After some coaxing and extreme pressure I got her to give me a blow job in my car. Just as I imagined she did a great job and her big lips felt great. I shot my load in her mouth. She got me to shoot my load quick. By the time I parked at the restaurant she was swallowing my jizz. I thanked her and we went in and had lunch. Again on the way back I asked her for a handy or BJ and after a little pressure she agreed and quickly started and wrapped her thick lips on my dick. It was a little warm so I rolled my window down a bit. As I was pulling out of the parking lot I rolled the Windsor down the rest of the way. I group of people went standing waiting for me to pull out. There was some traffic and I was waiting. All of a sudden Jessica the girl giving me head looked up with her eyes and saw about 4 - 5 people staring at her as she bobbed up and down on my cock. She was so embarrassed. I had the back of her head with my free hand that was not on the Steering wheel. I got excited from them seeing her and I shot my load. Holding the backs of her head she swallowed and licked up what spilled out of her mouth. She was mad at first then got a little excited and she ended up fucking me in the front seat. I took her home Friday after work and gave her a proper fuck. Today is
Monday and I have been in her since Friday. She told her BF that she was spending time with her parents this weekend. She spent it half naked most of the weekend. I enjoy her lips and thats why I continue to see her. I know it’s fucked up but she sucks a good dick

Her First Black Cock

When I lived in USA I dated a very vanilla girl. Young. I was 27 and she was 19. Loved sex and always told me to teach her and push her boundaries. I worked with a guy from Jamaica. As a straight guy, I have to say this guy was sexy as fuck. Tall. Chiseled muscels everywhere.

We were pissing next to each other one day and I caught a glimpse of his cock. The guy was hung like a fucking horse. Romandi has told me before that she is curious about interracial, but has never had the chance and is scared. I breach the subject with my friend and he is all for it.

That night I blindfolded Romandi. Told her another guy is going to fuck her. She believed we are role playing and it would be me. My friend was waiting and I let him in. Romandi was standing doggy style at the edge of the bed. He put his hand on her hip, grabbed his cock and started pulling it through her pussy lip and over her clit. Then he started entering her. Watching Romandi's lilly white, waxed pussy open up, being very pink and wet, and wrap around his cock was amazing. My cock is big. His cock was bigger. After pushing in halfway, she realized something was up. She had a spreader bar between her ankles and her hand were lightly stretched forward and tied to the bed. If she wanted to, she could have moved and gotten up, but she didn't. She kinda jerked, whipped her head around, then relaxed and moaned. She knew she just took someone else's cock.

As my friend started moving his cock in and out, Romandi lowered her shoulders to the bed and arched her lower back and hips. He started fucking her harder, holding on to her hips. Her ass was rippling and shaking as he hammered into her pussy. Big, D cup tits hanging under her shaking as she got railed. I asked Romandi if she was having fun, and she just moaned. I indicated for him to flip her over. He loosened her hands and manually flipped her over. On her back, he pulled her to the edge, took off the spreader bar and put her feet on his shoulders. I was amazed at how easily Romandi took his cock. He later said she was the first woman that could take him from get go without having pain. This guys cock must have been 28 or 30cm and as thick as a coke can. She said later that the first few minutes was painful, but she wanted to put a show on for me and after a few minutes it really did start feeling amazing. Watching his thick cock pulling out, her pussy lips pulling out with it, grabbing his cock, was hot as fuck.

I was jerking off furiously. Precum dripping out of my cock. After a while, being slow and silent, I reached over, took hold of her blindfold, and pulled it off. The look on her face when her eyes opened, focused on him and then realizing what's happening was priceless. She knew there was another man fucking her, but not a 190cm tall, 95kg, black as night Jamaican. She screamed, kinda attempted to scoot away, looked over, saw me with my dripping cock in my hand and then fell back into the bed, moaning. She orgasme shortly after and squirted so hard that a a stream of her cum hit him on the chest.

After that, I got involved. We fucked her for hours. Sometimes just him. Sometimes me. Sometimes both. She could not take his cock a anally, it was simply too big. We did dp her. Me in her ass, from behind, her sitting on his cock.. She came so hard, she passed out several times. We both creampied her a few times.

Before he left, she sucked his cock for the first time that night. She struggled, but made it worked. She then shocked me. I used to cum in her mouth all the time ,but she always spat. She never swallowed. I saw his cock pumping up, the veins straining along his shaft. As he started cumming he screamed fuck loudly and pumped cum into her mouth. Some escaped, running down his cock, but she swallowed his cum. Without hesitation.

We fucked her several times after that. Eventually I came back to SA. I lost contact with her eventually, but for a good 2 years, they would regularly send me pics and videos.

She got a queen of spade tattoo above her pussy later. She said she wanted all black men to know that she loves black cock and they are free to approach her. She is married to a white man.

One thing that stands out for me... He wanted to cum on her tits. She sat back, leaning on her arms, big tits proudly and heavily hanging. I was sitting next to her. Watching. She looked at me and said it will be hot if I jerked him off. So I did. I simply reached over, grabbed his cock and jerked it until he sprayed her with a big load. Her tits was covered. She even took some on her cheek. It was fucking kinda hot. Feeling his rock hard cock, the veins and then the edge of his cock head slipping through my hand and then the pulses as he came, was hot

Thank You Mrs R

In junior high I had this teacher names Mrs Rodriguez. She was married hard dirty blond hair taller then average maybe 5 foot 7 nice tits small waste big hips and a big ass. She wore glasses was very pretty but every boy did what they could to cop a feel or try and get as close as we could to her ass. She seems to always wear jeans or leggings that made her ass pop.
Some times a kid would get in trouble for accidentally sliding his hands across her ass cheeks. Sometimes i guess depending on her mood she would not say anything. I know that a few times i had a handful of ass and never even got a reaction. Fast forward a few years and I’m a junior in college and am back for Christmas break. I hook up with friends that are back as well and out we go. Our town is a decent size and there are plenty of places to go. We decided where to go and hit there happy hour. There was a few Christmas parties and I noticed a dirty blond with a big ass at the bar. I knew who this was and made a straight line towards her. She is super flirty as I approached her. I chatted her up for a bit buying her a few more drinks. Her party is winding down and one of her friends lets her know that she is leaving. That was her ride. She tells her that she is good and made arrangements to meet so and so here. So she would be ok. The girls says ok then see you on Monday. We were in the corner of the bar kind of private we didn’t know anyone that was left except of my buddies at the bar. My tab was laid I text my buddy I’d see him later. The last thing I text him was il send you pictures of Mrs Rodriguez in a bit. She walked out with me I had agreed to take her home. When we got to my Tahoe we ended up kissing and she was in her blouse and thong within minutes. I had my phone out and recorded her taking her pants off and got to see her ass spill out of her jeans. I took my time and put her ass up in the air and proceeded to eat her out as she lay face down. My phone recorded the whole thing I propped it up on my phone holder and it had a clear view and was able to pick up he words of please fuck me. I proceeded to let her grab my cock and guide it into her sweet little hole. It felt so tight. She rode me in the back seat and after a few pumps I would slide my middle finger into her butt. This caused her to move her hips faster. She must have been worked up because she started to shake and scream a bit as she came I sunk my finger deep in her ass. She said OH fuck I needed that. She gave me a kiss and told me that if I wanted her ass to take it. I flipped her on all 4s and slid my cock deep in on the first pump. I had a handful of her hair with one hand and with my free hand I was slapping one cheek leaving it bright red. We spent about an hour in my SUV and ended up taking her home. She had me drive by to make sure no one was outside the home. She told me that she was still married but would like to see me again. I left for school a week ago and we met up a few dozen times. I finally told her who I was and she was a little embarrassed. I was ramming her rear door and calling her Mrs Rodriguez. She got into it and started talking back. She is going to make the 3 hour drive and come and visit me this coming weekend. Il see if she will let me and a buddy double team her.

Lapse Of Judgement

Last week I was messing around with my boyfriend, well, he was fucking me, and his two roommates stumbled into the house after a night at the bar. We were in the couch and in a very compromising position. Yes, they saw everything!!!

But it turned highly sexual very quickly. They outright asked my boyfriend for their own turns on me. I laid there trying to cover up with a pillow and all I could think was ‘holy fuck, I am going to get gang banged right now!’ My pussy started to spasm and my nipples went rock hard. I was in trouble if my boyfriend gave these guys permission.

Gabby….’do you have any objection to them fucking you’ came out of my boyfriends mouth and all I could say was if you don’t, then I don’t.

No sooner than those words leaving my mouth these guys were all naked and pouncing on me. They found my pussy and laughed at how creamy I was. ‘Look, her lips are covered in cream and it is dripping into her asshole!’ I was sexually humiliated and completely turned on at the same time.

For the next three hours these three guys fucked me like a whore. The drunk guys were semi hard but still able to get sucked and to fuck. My boyfriend has his turns too. The night ended with my boyfriend cumming a couple of times, with the other two teasing me that I could not get them to cum…..of which I did after some prolonged sucking and jerking.

The next morning I felt uneasy about it. My boyfriend has been cold since that night but he has said they want to do me again. I want it again, but I want my boyfriend too!