JamesDean69

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Gender: Straight Male
Age: 35
Relationship Status : Not specified
Profile Visits : 474
Number of Comments : 8
Number of Confessions : 7

JamesDean69's Favorite Confessions:

I Can’t Believe It Happened

Last night I went out for a happy hour and stuck it out with my work besties. There were only a few guys who wanted to stay. One of them was single, well call him T. He’s super fit, usually fills out everything he wears with his muscles. All the girls were practically drooling over him. I see him around at work all the time but we mainly just pass by and small talk. Some of the girls left to use the bathroom to talk about drama and all of the guys had left leaving us together. We sat down on long patio sofa the bar had. He kept complimenting me throughout our convo and pointed out that I had a nice figure and sexy skin tone. I started to melt in his presence and realized I was in a bad spot. My boyfriend called me, I was thinking it was a great time to leave when suddenly I start feeling Ts hands down my back. I looked around and we were still alone. I wanted to tell him to stop but he leaned into my neck and said I can take you home, he starts squeezing his crotch and brings my hand over to his thigh. I was so turned on and hung up on my bf. He start running my hand up and down the outline of his cock. I was so wet, I wanted to just lean over and suck him off. He felt bigger than my bf and thick in my hands. I was pretty much in a trance until we heard the girls come out and readjusted to make it look like nothing happened. No one noticed but when we were all about to leave he squeezed my ass when no one was paying attention. I went home to my bf with a gf who offered a ride. I wanted T to take me home and pin me up against a wall. I’ve never felt a cock that big before. I don’t know if I can resist next time.

Daughters Gift

For my 48th birthday, my daughter got me a 2 hour massage with her therapist (also her best friend). I have had two massages my entire life and both were okay, but nothing to keep me coming back.

I make the appointment for a Friday night. My thought was I would be able to recuperate on Saturday if the massage did not work the intended magic. When I got there, Abby greeted me and led me to the massage room. We talked a bit about where, how hard, any problem areas, etc. Abby then left the room. I got undressed and laid on the table face down. It was warm, soft on the top, but firm under. I am curvy and I felt like it was wide enough for my motherly hips.

Abby returned, adjusted the sheet, told me to relax and enjoy the next two hours. She mentioned I was the last appointment of the night so we had no reason to rush. She started with the sheet on and moved her hands the full length of my body. I could feel little releases with each stroke of her hands. Shortly after, she rolled the sheet to just above the crack of my ass and began working on my back, neck and shoulders. So good, so deep, so releasing. She got my neck to crack!!!!!

She then went to my legs. She moved the sheet to one side and did one leg at a time. Her hands went as far up as my legs were open. Each time, seemingly involuntarily, they opened more with each stroke. That is when she put the cushion under my waist. This immediately stretched my lower back and legs but it also exposed my pussy. I did hesitate, but Abby’s hands were in control, so I went with it. She eventually pulled the sheet off (with my permission) and the massage really started to loosen up my lower back. It was like she unlocked twenty years of pent up hell. She massaged my ass too and that released the tightness in the back of my legs.

I am in heaven and then she slips her fingers down this inside of the crack of my ass, just barely grazing my rosebud and my pussy. The energy bolted all over my body. ‘Are you okay Britney?’ Yes, I am good was my response. She did it again, but deeper. Again more energy. She did it one more time - her finger found the inside of the folds of my pussy and I thought my body may catch on fire. So much energy. So much anticipation.

Are you okay Britney? All I could do was say uh huh.

‘Take a deep breath for me and relax’. With that exhale, Abby’s finger slipped all of the way into my pussy. My hips lifted. My loins roared. The energy found every nerve in my body. I whimpered ‘oh fuck’ and tried to catch my breath. ‘Relax and breathe for me Britney’. In went another finger. The oil made my pussy completely open, inviting and vulnerable.

Take a deep breath, feel my hand on your shoulder…..in went the third finger. ‘Fuck!’ One word! Fuck.

Abby started to finger my pussy - first slow then faster. Her thumb was pinned to my rosebud and my clit was getting battered with the last finger. ‘Keep breathing Britney and let it go.’ She rubbed my back softly, encouraging me to release. Then she did the most stimulating thing that has even been done to me: she leaned into my ear, gave me some soft, warm breathes and she says ‘now please release the pressure and cum for me’. She pushed all three fingers in and up, hitting my SPOT. ‘Oh fuck, I am cumming!’ And with that, I came like I have never cum before. It was hard, head spinning and fully releasing.

She never stopped. She kept saying there is more in there. Release it. She made my pussy cum 6 times that day, including two while I was on my back. When I got home, my daughter was waiting for me. She knew so I told her everything. She admitted to getting the same treatment from Abby when Abby was in massage school and has been enjoying their sessions since.

I have gone back 3 times already and I cannot wait for the next session in October.

Hot Tub Cum

My husband and I are in the hot tub one night. We are literally unwinding from a very stressful month, which included a new job for me, a lot of work for our plumbing company, a new granddaughter. Yeah, lots going on.

I feel his hand rest on my thigh….then higher…..then my lower stomach. Instinctively, I spread my legs open as wide as I could and laid my head back. Without hesitation, we goes for my hairless pussy. He immediately finds my always exposed clit and works her slow then more rapidly. I am one big nerve….fuck. After a few minutes of being on the edge, in some guttural voice I say Jeff, fucking finish me already. His fingers pinned my clit to the bone behind it with his knuckles and sent me sinfully over the edge. I came like never before. But he never stopped. He just kept on pummeling my clit, relentless knuckle stimulation….another hard cum. He is working on the third cum and he says he has something to ask me. Gutturally, I say anything…just do not stop. Anything???? Yes!!!!! Anything you bastard!!!!

I want to watch Chris fuck you!

What? Fuck…. Fuck….fuck….the bastard finally slowed down so I could talk. Chris is a very large black client of ours and he is always flirting with me. I asked why? My husband said he is always asking me to sleep with you and I think it would be hot. He gives me no time to answer and blasts his knuckles into my clit. Fuckkkkk….no up and down and no left to right….just rotating hard pressure. I could feel my pussy creaming like never before. Jeff, do not tease me. Please finish me. I will do anything. I need to cum. Anything???? Yes, anything!!! I am right there now and I start to cum. He says say it….say I will let Chris fuck me!!!! This was the hardest and longest cum I have ever had! Out of my mouth comes I want Chris to fuck me! It stopped seemingly five minutes later. My head was a blur, my body was tingly. My pussy was creamy. My head is laid back.

Jeff says…anything? Yes, anything! I just want that pleasure again soon. Even Chris? Yes, I want Chris to fuck me. Set it up.

Later that night, it occurred to me that I used the word WANT. Did I want Chris to fuck me or just allow him to fuck me? This one word distracted me all day, to the extent that I felt bad about it. After dinner, I mentioned it to Jeff. His response was true to who he is (just the facts he always says) - do you want Chris to fuck you? My response was yes, I would thoroughly enjoy Chris fucking me.

I Feel Bad That I Cheated But Found Something Out

Hi, I'm a 35 year old married female and have been married for 10 years. My husband has a small penis about 6" we have great sex and I orgasm easily when he eats me or uses a vibe on my clitoris. I have never cheated on him till one evening I was out alone and stopped at a bar for a few drinks, I guess the alcohol went to my head and I started having a conversation with a man at the bar, one thing lead to another and we were in a motel we were kissing and touching each other and were naked in minutes he penis was very large about 8" and very fat after a lot of oral he entered me the feeling was so exciting he only made about 3 or 4 pumps and I had a different type of orgasm there was no clitoris stimulation at all it was a vaginal orgasm only one that I ever had and was great feeling. After another 2 orgasms I let him finish in my mouth. I cleaned up and went home I felt bad but didn't say anything. I don't think I'll do this again because I'm in love with my husband and he doesn't deserve this

I Did It.

I can’t believe what I just did. I am a 41 year old married mother of 3 and i am sitting on my flight home to my family with another mans cum in me. I had to travel for work as occasionally happens and this time I met a man who was staying at my hotel. The first night he sat by me in the hotel restaurant while I ate my dinner at the bar. We started chatting, discussing our reasons for being in SF and our families (he is married as well) His name is Miles and he is 53. His kids are all out of the house and he travels for work regularly. He was charming and I admit that I enjoyed his attention but nothing more happened. The next night found us in a similar situation and we chatted and I felt so comfortable with him. After dinner and a few glasses of wine we said our goodbyes. Last night was our final night and again we ended up sharing dinner and more glasses of wine. This night however, when we said our goodbyes he gave me a hug then leaned in for a kiss. I was stunned and before I knew it i was kissing him back. When we broke our kiss he told me that he wanted me to come to his room. I was holding his hand and ready to say yes when my phone rang. It was my husband and I was immediately filled with guilt. I told Miles was sorry but I couldn’t cheat. I said goodbye and went yo my room talking to my husband while feeling guilty. In my room i undressed and found I was soaking wet. My panties were shear they were so wet. I am glad I never got his room number or I would have gone to him. Instead I used my fingers to bring myself off several times but I still felt empty. That brings us to this morning. I am at the airport waiting for my flight all of a sudden Miles to s standing in front of me. I look at him and he begins to apologize and offers to but me a coffee. I agree to the coffee and while walking to the coffee shop I admit to him that if my husband hadn’t called I would have gone back to his room then I further admitted that if I had known his Room number I would have gone after getting off the phone. He said something about missed chances then asked me what about now. I laughed and said right here in the airport. He smiled grabbed my hand and said he had an idea. I just let him lead me by the hand to a family bathroom. We entered together without looking around and as soon as he locked the door i was in his arms kissing him. It didn’t take ling for my pants to be down around my ankles and I was bent over the sink. When he entered me I came immediately. I was ready and wanted this like nothing ever before. He quickly set a pace that had me in heaven. All too soon though I felt his pace quicken then he tensed up and unloaded inside of me triggering my final orgasm. We stayed connected for a few minutes while we caught our breath then he slowly withdrew. As soon as he was out I knew I would miss his cock. It fit perfectly and now I was empty. We didn’t say a word as we pulled up our pants. We then left the bathroom and he walked me to my gate. My flight was boarding and he asked for my number. I kissed him one last time and told him that it wasn’t a good idea. I would want to see him and do it again and that was a bad idea as I didn’t want to risk my marriage. I said goodbye to miles and here I sit waiting to taxi out with his cum inside of me. I can’t believe I did it and right now feel no guilt but I think that will change.

The Aftermath Of Jackson

So I told my husband about what happened with Jackson while I was on my business trip. Obviously he was and is still not happy. I guess I get what I deserve. I explained that I tied so hard to deny the desire at each crossroad but it just continued to smolder deep within my sex. Jackson had a smoothness to him that made me feel calm, relaxed and safe. Jackson also had an aura that made me feel wild and free and adventurous and ultimately filled with sexual desire. When I was walking down the hall the first night, I felt like I was being pulled, like an out of body experience. When he opened the door, his nearly naked body took me by surprise but also stoked an incredible amount of heat between my legs. His touch, his kissing, his passion were all unmatched by anyone in my sexual past. His cock, as I noted previously, is the true definition of a big black cock. Long, thick, very dark black, huge hanging sack. It just hung there when semi hard but once it was fully hard it stuck almost straight out from his groin area like a steel beam that would hold up a house. It said suck me, it said I am going to fill you, it said I am going to fuck you like never before. As such, I gave up my pussy bareback for him, without any reservation. Being 57, he is over twice my age. I could say he preyed on me, but make no mistake, I was a willing participant. I allowed him to sit next to me, I allowed him to pay for dinner, I walked to his room, I allowed him to penetrate my white pussy. But ultimately, the worst and most challenging part for me was that I went back the next two nights. I went to his room, knowing he would fuck me until I could not walk. I knew his cock would fill and stretch my young white pussy to the max. I knew his stamina would create long, deliberate pounding on my cervix. He knew exactly what to do: he knew when to pound, when to spank my ass, when to pull my hair, how to use words to enhance the experience, when to change to another position, when to go easy. He would be in the throws of pounding me and he would say things like do you like that big black cock or are you my white married slut and many other things - and they all just stoked the burning desire even more. His cum was thick and delicious. Over the few days with him, he came (maybe) 10 times, mostly in my mouth and on my body. He never came in my pussy, but I probably would have said yes if asked.

I have watched more interracial porn in the last five days than all of the porn in my entire life. I am a white married woman with an incredible desire to be taken by big black cock. I do not see how this is possible by the actions of one man, but it is true. I love my husband, but he cannot do what this man did to me. Jackson fucked me ‘good’ over and over and over. He left my pussy loose, hot, needy, but curiously fulfilled.

My porn experience has lead me to this: I seem to be a hotwife or maybe even a queen of spades. I do not believe my husband will ever be cucked, but it is to be seen whether or not my desire for big black cock will be satisfied again in the future. As I type this, I have made my pussy cum twice and there is more there for the taking.

What did this man do to me that I feel like I have been changed forever?

Divorced And Alone I Enjoyed One Night With My Neighbor

I live alone in a condo in a nice complex. Down below is a young couple. I envy that they are together. When the opportunity presents itself we are always quite cordial and exchange pleasantries and I wonder just how he makes love to her, of course wishing I had someone to make love to me.

One day I found him alone, he told me his wife had gone home to see her parents and celebrate her grandmother's birthday. I invited him to come by for dinner, and have a hot meal and he accepted. Why that night I behaved like I did I don't really know. I wore a dress without panties, shaved completely, something I did from time to time. I decided that a bra was not right, he would want to enjoy my breasts and my dress tight up between my legs. He was a man after all, if nothing came from it that was fine with me, but that night I could show him that I was a woman.

We had a pleasant enough dinner, talked current events and his wife's family so far away, and he told me his family was also far away, in Montana where he grew up. After dinner I told him that if he didn't mind, I would really like to suck his cock, I hadn't held a cock is such along time. He was hard, my heart was in my throat as I put my lips on his cock and filled my mouth. I stroked him as I sucked him and he got harder and harder. I could feel him start to twitch and shove his cock at me, so I stood and lifted my dress off and stood in front of him and asked if he wouldn't rather cum in my pussy than my face.

I lay back on my bed, and spread my legs wide open, you know, with my knees resting on the sheets so he could get a full on view of my open pussy. I invited him to lick my pussy and let me feel like a woman. His mouth was strong and his tongue searched for whatever was in his mind, I guided his index finger to my clitoris and arched my back to feed him better. I came, it was a shock to me, it was violent, I tossed him off and he put his hand to my throat and skewered me with his cock holding me down so I couldn't move.

I don't know if he ever told his wife about that night, but I remember it so well. One night, that's all but what a night it was for me.

First Affair

I am Mikayla and I am from a large east coast USA city. I am married (3 years) and I have a pretty normal life and a pretty cool job.

Last week I cheated on my husband. I was away helping my boss close a very very large account. He took me and our top sales executive to Seattle to help finalize the deal.

One evening I felt cooped up in my hotel room so I wandered down to the hotel bar. It was sprinkled with a few couples but mostly it was single men.

Like a beacon saying I am available, I sat at the bar and had a Jamison. It was a challenging week leading up to this week and the deal was planned to close on Thursday. We had prepared very well so I figured a drink or two would not hurt.

About 15 minutes later I decided to order a quesadilla. As I finished ordering, the bartender gave me a drink, pointed to the man in the corner and said this is on him. I turned, nodded a thank you and smiled. Three minutes later, an older, distinguished, well dressed black man was standing next to me. I offered the stool next to me but I made sure he understood I was married.

He nodded and took the stool. As he sat, his pants barely covered the largest cock I had ever seen. It was extremely difficult to miss, even for a much married woman.

We talked, eventually my quesadilla arrived and I offered Jackson (my new friend) some of it. The conversation flowed so easily, like it was meant to happen. He was confident, happy, single, well to do, hung (lol) and he had my attention. My husband popped into my head a couple of times but I will tell you that Jackson had me distracted. The quesadilla turned into cheese fries and a drink or two more, but I could feel my brain and pussy starting to fail me. I made the decision to go back to my room and calm down. Jackson paid the bill and he led me to the elevator. As we got into the elevator, he pushed the button for the fifth floor and asked what floor? I said the same (fifth). That was weird. We both get off the elevator and start walking down the hall. This is bad.

As I stop at my door, Jackson continues down the hall and says room 524 if you get bored. My heart races, my brain goes into hyperdrive and my pussy is on fire.

‘Just to inside your room and go to bed Mikayla!’

As I started to get undressed, I could feel and smell my sex. She was certainly cranked up and I would have to do something about it. I texted my husband (3 hours difference) and said good night.

As I took my panties off, it was impossible to miss how creamy they were. Damp and creamy. My lips glistened with my cream. My clit, which is the exposed kind, seemed to be looking at me and wondering what now. How did this man do this to me? As I stood there, I just imagined what could be. I took a deep breath, put on a t shirt and running pants and opened my door. Good, nobody in the hall. As I walked to room 524, my body has on fire. If I walked in that door, this man would have me and I would be powerless to stop him.

Knock, knock. I heard the tv get quiet and foot steps coming toward the door. As the door unlocked and opened, standing in front of me was 6’ of problem, only dressed in a tight fitting pair of athletic boxers. Fuck, I was in trouble.

He greeted me, led me in the room, kissed me and immediately started to undress me. More kissing, more playful touching. He kissed my neck, chest and nipples. I was incredibly horny at this point. I reached for his cock, barely held behind his boxers, hung like nobody I had been with before. As I reached inside, I could not speak. This was the true definition of a big black cock. My hand barely fit around it.

I sat on the edge of the bed, brought it to my mouth and started licking it. Up and down; sucking the tip; licking his hanging ball sack. When I opened my mouth, he helped slide his cock in it, hitting the back of my throat. This made my eyes water and my throat create some thick saliva. I knew why I was here and I planned to give the cock my best. I worked it hard, deep, sloppy, wet. The saliva was all over my chin and my naked chest. The sheet under my ass was a smoldering hot and creamy mess.

Eventually, he leaned me back and attacked my sex with his tongue. The magic this man did on her sent her over the edge in record time. I came, hard, guttural, deep, powerfully as his tongue plastered my clit and lips. It was then I looked up at him, horny and desperate, and told him to fuck me.

He stood up, stroked his cock a few times, rolled my legs so my knees were touching my nipples and entered my wide open pussy. He filled me to the hilt. Deep, stretching, filling.

He fucked me for a few minutes and I had my second orgasm. Again, strong and powerful. This time, just as I came, he pulled out and I squirted all over the bed. He fucked me like that all night. I left at 6:00 the next day. I slept in room 524 the next two nights.

First Time

My wife and I have been married for 15 years. We have a very normal, middle class life. We do not have money problems, we have good kids and a nice home. Basically, living the dream.

About a month ago we were invited to a party at a friends house. That party was last night. I am a smart guy. And I will not tell you I am naive, but I completely missed the fact that it was a swingers party. When we walked in, everything seemed normal. After 15 minutes or so, Mark started inviting us to their other friends. Still nothing and no indication of this being a swinger party.

About an hour into the party, Christina (our friend and host) yells ‘game time!’ and every scurries to find a place in the den. We follow like sheep, different but nothing indicating anything. Mark sits next to Carla (my wife) and says you do not need to do anything you do not feel comfortable doing.

Carla turns to me, calm and cool and says Curtis, this is a sex party. I was like no! And she says just be ready…just be ready and we can take it minute by minute.

We get introduced again and Mark says go easy on them as they are first timers. Now I am starting to get antsy. I do not want to cheat on my wife nor be cheated on but is it cheating in this setting? So much floating around my head!!! Carla asks if I am alright and I responded with I guess.

After some other people answered some questions and did some minor ‘sexual interactions’ it came to Carla. ‘Have you ever been with a woman?’ Without any hesitation, none whatsoever, Carla says yes, in high school and in college. My head went cloudy and was spinning at the same time. I looked at her and said really??? Yes, Curtis a few times. I swear, my dick went from ice bath soft to raging hard-on in about 12 seconds. WTF!

Christina says out loud ‘are you okay Curtis?’ And hesitate and Carla says ‘he is okay!’

My turn - would you sleep with the woman or women wearing red tonight? Two women and yes to both….but how the fuck do I answer this? Carla says, in a very stern tone, just fucking answer! Again, WTF! So I answer yes to both. Mark says Carla pick a number 1 or 2 and she answers 2. Apparently she chose Corrie. Corrie stands up, comes over to us and says yay, it is playtime.

Carla, Corrie, me and Corrie’s husband (Bill maybe) all walk out of the room and find a bedroom. As we get there, Corrie stops and says we do not need to proceed. Nobody will shame you or anything. Just be okay with this before we walk through the door.

So I am semi hard and Carla says we are good and we proceed. I did not get an opinion. My head is spinning, Carla controlling this situation with Corrie. Before I know it we are undressing. Bill literally has a horse cock! Where the fuck am I is running through my head.

Corrie leads Carla to the bed, kisses her and finds her pussy with her hand. Carla has the look of pure evilness on her face. She smiles and tells me to touch Corrie as Bill starts touching Carla. I go along until I feel Bill’s hard cock brush my leg. Carla looks at me, stops Corrie and says ‘stroke his cock, now!’ Corrie looks at me and says ‘he won’t bite, just touch it.’

My head is spinning, my cock is hard as a fucking rock and I say Carla, really? Her response was direct and unwavering ‘do it now!’ I take a deep breath and grab Bill’s cock and stroke it. Without any hesitation, he grabs mine and the women continue to kiss and play with each other. Corrie was the first to cum, Carla says ‘good girl, now take Curtis’s cock and stroke it.’ Me feeling better about this I say ‘thank you, this is better’. Carla laughs and says ‘suck his dick!’ I was like no. Carla looks me straight in the eye and says you will not get anymore pussy if you do not suck his dick right now. Again, WTF!

After about a minute of debate, Corrie stops stroking my cock and Carla says that she is growing impatient. Bill says nothing, Corrie says just watch me do it and then follow me.

About three minutes later Carla says enough, it is your turn and she pushes me to my knees. She grabs Bill’s dick, puts it in front of my mouth and Corrie pushes my mouth on Bill’s dick. I nearly gagged. Out of nowhere, Carla starts coaching me in what to do and how to do it. I am down there 15 minutes and Bill says he is getting close. Carla says ‘good, he will swallow it all.’ For the first time in my life I was the submissive. Carla was the dominant. She can be in real life, but this was over the top.

Corrie is kneeling next to me, I am bobbing in his dick and he says the most intimidating words ‘I’m cumming!’ Carla say ‘swallow it, Corrie hold his head’. I had no choice!!!

So here I sit, saying the same thing over and over, WTF! Carla, my bride, wife and mom to my children, was a dominatrix and I never knew it!

I Don't Mind Being A Cuckhold

My wife is upstairs in the bedroom with her boyfriend. Whatever he is doing to her must be right as I can hear her muffled moans and cries of yes yes.

I have ED and told her to find an outlet for her desires. She thought it funny at first then she became a bit more serious, and started going out with her single girlfriend. It was just flirting at first but then I guess she had some chemistry with a guy had sex with him and it wasn't as strange as she thought it would be.

Now she has a forty year old guy that bangs her once a week and I find that her attitude has improved 100%.