Adult Confessions

Over 75,650 Adult Confessions Shared!

JackieDaytona3019

JackieDaytona3019 Avatar
Gender: Bi-Sexual Male
Age: 41
Relationship Status : With someone
Profile Visits : 261
Number of Comments : 2
Number of Confessions : 10
About JackieDaytona3019:

Married, a Dad, nerdy, & kinky. Been a perverted deviant since I was 10 and have found my match with my wife. We’ve been in the lifestyle for a few years now and now I’m excited to share our experiences with you.

Confessions by JackieDaytona3019:

- Fetishes and Kinky Sex -
Bi-Sexual Male / 41

Last Saturday

The wife and I were returning from a work function. We had a few too many old fashioneds and got an Uber home. So wifey gets pretty rambunctious and handsy when she’s drunk.

So the Uber shows up, nice black SUV with a 60ish man driving. The drive is kinda long as we live in a suburb on the other side of the city from where the work thing is at, maybe 35 minutes. The issue is that the wife is frisky and has little to no patience on a good day. She’s kissing me while pawing at me and grabbing my junk through my pants. I know her pretty well by now so I know she’s gonna do something, I just don’t know how far she’ll go. So I just patiently wait as make out.

Doesn’t take long for her to start undoing my belt, and she takes me out. It was kinda awkward as the driver was fully aware and I didn’t know how he’d react. This is not the first or even 5th time she’s done this, and we’ve had a driver flip out on us. We haven’t used my Uber account since because of that.

Thankfully the driver just adjusted his review mirror to get a better look and never said a word. So I got a nice sloppy blowjob from my frisky wife, as this older white guy watched. It’s too bad that my wife didn’t have another drink or two in her, cause she probably would’ve let the driver fuck her if he had a condom on hand.

1
# 74250 - by JackieDaytona3019 / October 25, 2024
- My Family -
Bi-Sexual Male / 41

Helped My Son Lose His Virginity

I have a local Asian massage parlor that I visit once or twice a month. They have nothing but tiny Asian women working there and I have a huge weakness for petite Asian women. In all seriousness I highly doubt any of them are over 5’ or weigh more than 100 lbs. $100 to fuck a tiny little Asian woman is more than worth it, even if I only get a handjob.

When my son turned 16 I told him that I had a special surprise that he couldn’t share with his mom or sister. My wife is fully aware that I fuck these massage ladies and she doesn’t really care, to be fair I don’t mind that she’s fucking her workout instructor or the kid she’s teaching piano to. However she wouldn’t be happy that I took her darling son there.

I took him the day before his birthday, when his mom and sister were out doing one of their “shopping therapy” days. So we get in there and the ladies line up like a lewd buffet, all of these fit young petit Asian ladies wearing next to nothing. My son chooses my suggestion, she’s maybe 20 and really knows what she’s doing. I gave him one of my ed meds and paid for 2 hours plus double for a tip. Afterwards she told me that not only is he hung like I am, but that he went 4 rounds with her.

I never took him back but have been told by the ladies there that he has returned a few times and that they enjoy having him as a client. It makes me proud that he’s able to come here and do this while still being so respectful and polite to the ladies.

1
# 74198 - by JackieDaytona3019 / October 23, 2024
- Fetishes and Kinky Sex -
Bi-Sexual Male / 41

Wife’s First Gangbang

This happened about 2 years ago or so. At this point the wife(40F) and I(41M) have been together about 19 years, married for 16, swinging for 3, our daughter had just left for college, our son was a hs junior.

At this point me and my kinky wife have done a lot of experimenting together. We’ve had several threesomes with men, women, and transgenders. We have dabbled in water sports, bondage, being both dominant and submissive with each other, done gloryholes, anal, atm, pegging, public sex, swapping, etc. What we haven’t done at this point is a gangbang. She’s always wanted to and it’s her go to for porn, however she always lacked the courage and confidence for it.

She finally worked up the courage and we put up a CraigsList ad. We got 6 men who were interested, above average in size, and were willing to provide proof of being STD free. In the end it was 5 white guys, and a black guy. Funny enough this broke with stereotypes as the black guy had the smallest cock. We got a hotel room and set it all up. Put out extra towels, lube, drinks, snacks, sex toys, etc. We even shared my ed meds with the group.

She was wearing some black lingerie that she bought for the event. Matching Lacey bra, panties, stocking , & garter belt. She was even wearing a new buttplug with a purple j*wel on it. They guys all arrived around the same time, and thankfully no one catfished us or brought a friend.

We kicked it off by having her kneel in front of them all for a nice blowbang. Wish I had recorded it because she was living one of her biggest fantasies and it showed, she had so much excitement and enthusiasm for the 6 cocks in front of her. One of the guys was built like a pringles can and she had a lot of fun struggling with her that monster. Easily the biggest she has had at that point, or even now I believe.

Soon enough she was on all 4s on the bed and was being spit roasted with jacking off 2 cocks. I sat in the corner and just watched as she lived out her biggest fantasy. The best part was when she sat down on the Pringle’s can dick and rode it. I’ve never seen her cum so much with such rapid succession. Easily like 5 big orgasms, one after another. She was a beautiful quivering mess. Then the one of the guys replaced her buttplug with his cock, and three others moved up so she could jerk them off and blow them.
I kept the 6th guy hard as she was too busy, and he ended up joining in when the guy fucking her ass finished first.

This went on for about two hours, and by the time it was over each guy had cum atleast 3 times and she was covered and filled with cum. They guys left and I carried her to the shower of the connecting room, leaking cum all over me in the process. I gently washed her wore out body and then laid her down. It’s kinda amazing how their cum got everywhere. It was in her hair, in her armpit, inside her ear, between her toes, in her bellybutton, etc.

It definitely took more out of her than she thought it would, it took like a week for her to fully recover. Thankfully the kids believed us when we said that she had the flu lol

Since then we have done it two more times, last summer she took on 4 guys, and last month she had 8. Chances are she probably wont do it again for quite awhile. The recovery period is rough on her, especially after this last one. Most of the 8 were literal frat bros. Those kids are like the energizer bunny. They just kept going and going and going. I forgot how much stamina boys their age have. They really wore her out.

0
# 74197 - by JackieDaytona3019 / October 23, 2024
- Gay Stories -
Bi-Sexual Male / 41

First Time I Bottomed

About 20 years ago I was freshly separated from the Marine Corps and was figuring things out. I was strapped for cash but really needed a massage. So I went on Craigslist and found an ad for a free massage by someone going to massage school or something. I messaged him and set up a session at his place. I’ve had a handful of experiences with other men but nothing really substantial, just a kid experimenting. I suppose he was an attractive guy and he had pics of his wife and kids all over. He was middle-aged, white, Dad bod.

The massage itself was fantastic, he knew what he was doing and he had the right touch. I had to stop myself from making some very unmasculine sounds as he rubbed me .
It started out very professionally, but slowly he pushed the boundaries. He did the massage in old basketball shorts and a tshirt, but then he took his shirt saying that he didn’t want to stain it from the oil. For the same reason, he wore old ratty basketball shorts, ones shorter than I would’ve wore.

He didn’t have a traditional massage table, so I didn’t have one of those face holes to put my face in. Due to that I was eye level with his erection that was very visibly growing in this light gray shorts. so the whole time he was massaging my back and shoulders. I was trying very hard not to stare at his erection. He did a fantastic job doing my back,

He accidentally squirted too much oil on my lowerback butt area, and we had to discard the towel over my butt. He offered to rub it in and it felt so good and so shameful at the same time. He primarily focused on my cheeks, but he definitely put some focus on my balls and butthole. I was so ashamed for enjoying his finger circle my butthole, I just laid there and silently let him do it. In hindsight it is so obvious that it was on purpose but at the time I was oblivious.

After he worked away the oil, he just kept moving along as if nothing happened. Moving down my legs, doing my feet in a way I never knew I needed. He then had me flip over fully exposing my erection, But he acted like it didn’t exist and started working on my shoulders and chest. This is when I discovered that I do in fact enjoy my nipples being played with. It was so surreal having his erection inches away from my face and mine angrily pointing straight to the sky, and neither of us acknowledged either one of them. We continued on this way, with him giving the best massage of my life and the both of us pretending that nothing sexual is going on.

When the massage was over, he moved aback up to my cock. Slowly circling in and teasing my balls and shaft with occasional touches. As he did this he brushed his cock up against my hand, and I pushed back. Apparently my direct touch was what he was waiting for, as he pulled his waistband down and put his cock in my hand. It was a little smaller than mine which I was thankful for, as it would’ve been much scarier if he was as big and as thick as I am.

While I touched his cock he stroked me a bit, but with very frustrating light touches. He told me to roll over on my stomach, which I did without thinking. I guess I was in a bit of a trance and just did what I was told. Maybe I was always submissive or maybe it was conditioning left over form boot camp or maybe it’s both. The point is I rolled over and let him push his cock in my mouth without a single word or protest. It was like one minute I was getting a massage and then before I knew it, I had a strangers cock in my mouth. While I contemplated the sensation and taste of a cock in my mouth, he started dipping his finger into my butthole. My body betrayed me by lifting my hips off the table against his finger. I even enjoyed it when he called me a “good boy”. I got a bit anxious when he asked if I was still a virgin.

I distinctly remember making a whining noise when he pulled his dick out of my mouth. Again I said nothing, even as I watched him roll a condom on and get behind me on the table. He rubbed my lower back and told me relax as he pushed in his cock. It was uncomfortable but pleasant, and before long his balls were touching mine. I remember him saying “such a good boy, take daddies cock” as he started fucking me. He was only nice for about a minute, then he applied more lube and truly started to fuck me. It was so humiliating and so amazing at the same time. I mean I’m a fucking Marine who has deployed twice to war with an infantry battalion and here I was face down ass up enjoying getting my ass fucked, making girly noises , & calling a stranger daddy as calls me a good little boy.

I cannot believe how much it turned me on to be spanked and fucked by this older stranger. He reached around and jerked me off onto the table, which was probably the biggest load I’ve ever shot. Then he bottomed out in my ass, calling me a “faggot slut” as he filled the condom with cum.

We eventually met again once I came to terms with what happened.

3
# 74144 - by JackieDaytona3019 / October 21, 2024
- True Sex Confessions -
Bi-Sexual Male / 41

How I Met My Wife

When anyone asks The wife I’s official story is that we met on plenty of fish and hit it off right away as we recognized each other from when we briefly crossed paths at MEPS on our way to Boot Camp.

While the part about recognizing each other from the MEPS station i Actually happened, the truth is we met on the craigslist personal when I put out an ad for a submissive fuck buddy. When we met at the bar, we. immediately recognized each other. The plan was to meet a few times, However, I ended up for fucking her in the parking lot that night. Right over the hood of her car. After that we met up quite a bit, despite the fuck buddies we hung out quite a bit and were staples in each other’s barracks room.

I was having the time of my life as we had just gotten back to our second deployment and I had about nine months to chill and fuck around before I got out. Apparently your unit doesn’t give a shit about you if you’re not to deploy with them. She was more or less in the same boat, so we had a lot of time to meet up and fuck. She’s pretty submissive and went along with everything I wanted. Never thought I would find a woman willing to give me a blowjob while I’m taking a shit, enjoy being shared, being pissed on, would get off on pegging me.

She’s a sexy little freak who’s willing to try all of my messed up ideas and fantasies at least twice. I never would’ve thought that a craigslist ad drunkenly posted when I was lonely, would end up with me finding a fellow Wisconsinite nerdy freak, or that they would end up being my soulmate.

0
# 74089 - by JackieDaytona3019 / October 18, 2024
- My Family -
Bi-Sexual Male / 41

My Daughter

I have been blessed with a tight sexy daughter who is the spitting image of her mom. Those two are as cute physically identical as you can get and have been freely swapping clothes since our daughter was 17.

I have been painfully aware of our daughter’s development ever since she was 13. My wife picked up on it after we took our daughter to a lake at a state park. Apparently I was a bit obvious about checking out our 14 year old bikini clad daughter. That night as we were in bed, my wife copied our daughter’s voice and started calling me daddy as she stroked my cock. I nearly came right then & there. Since then she regularly dresses up in our daughter’s clothes, often using outfits that catch my attention. My favorites are her cheerleading uniform, old volleyball uniform, and this cute purple blouse black mini skirt ensemble.

What my wife doesn’t know is that as of this February, I am a premium subscriber of our daughter’s OnlyFans. And yes I stumbled upon it while looking up girls resembling my daughter. At this point I have spent a few thousand having her make custom pics and videos for me, with her dirty talking to “daddy” in each one.

One of my favorite things to have her do is sit back with her legs spread, and play with herself as she verbally confesses things to me. She’s told me all about how she lost her virginity, how many boys and girls she’s been with, her fantasies, and has even admitted to fantasizing about me and her mom and how she often listens to us at the door while we fuck. She even admitted that she knows me and her mom are in the swinging lifestyle.

It’s taking everything I have to not share this with the wife. She would completely flip out as it’s one thing to fantasize about her, but it’s another to have gigabytes of nude & lewd pics and videos of her. It also takes a lot to not admit everyone to my daughter, in my head she gets turned on by it all and we fuck however I would probably just lose her permanently.

2
# 74085 - by JackieDaytona3019 / October 18, 2024
- Gay Stories -
Bi-Sexual Male / 41

Me And A Buddy

Back in the day I served in the Marine Corps. During my last Christmas serving I was at a buddies house picking him up to go back to base.we had just gotten back from some podunk line dancing bar and were at his parents place in the hot tub with his older sister. She stayed for a bit then went to bed, we got a nice eye full of her in her bikini as she got up then she bounced across the snow covered deck to get inside to the warmth.

As soon as she left he stripped off his shorts and encouraged me to do the same, when I took them off he gave me shit for staring at his sisters jiggly bits.

I hadn’t done anything with another guy since I explored with my friend 15 years earlier so to be heist I wasn’t even thinking about anything other than the delightful way that his sisters glistening boobs bounced as she ran inside.

I was just enjoying the buzz and the hot tub, as big flakes of snow fell on us.

I forgot how he approached the issue but I remember being kinda some friendly pressure to engage in some mutual masturbation. Which was so weird as my friend was pretty homophobic. It was so surreal jerking off with him. We both sat up a bit so our cocks came out of the water, he looked to be about my size however he wasn’t circumcised like me. I remember being so focused on his cock then realizing that he was staring at mine. I came so hard watching him spray cum all over the water in front of him.

I wish we had more time to explore this, but unfortunately he was out 2 months later, and I was out 4 months later. Hard to stay in touch when you live in different states.

0
# 74082 - by JackieDaytona3019 / October 18, 2024
- My Family -
Bi-Sexual Male / 41

My Older Sister

When I was young I was quite the pervert, and took every opportunity to peep and spy on my older sisters. To be fair it’s not really my fault. I was 12 and they were 15 & 18 and were so tight and sexy. Looking back on it I realize they knew and were teasing me, there’s no other way for me to explain how often they showered with the door cracked open or how often they wore baggy shirts without bras or how often I saw camel toe or how other they bent over in front of me or how often I heard them masturbate or have sex through the walls.

I could go on and on about how I peeped on them, licked their dildos, or how often I jerked off in their panties and put them back in the drawer or how often I jerked off while listening to them through the wall but this is just to set the stage and isn’t what this is about.

The experience I wish to share happened when I was 16 and my oldest sister was 21. She came home very drunk after a night of partying and her upstanding friends spilled her onto our doorstep. I helped her in and up the stairs to her room. When we got in she immediately starting stripping her little black dress off showing her matching lacy black bra and panties. I knew the set well as I often jerked off into the panties.
I started to say something about how she should stop(while greedily getting an eyeful) and she called me out on peeping all the time and being a creepy pervert. She then smiled at me and sat back on the bed, and asked me if she was hot. She playfully and mockingly removed her underwear while taunting me.
To this day I still vividly remember her realizing that she had cum in her pussy and she said “which one of those assholes came in me?”. The fact that she was freshly fucked, filled with cum, and had multiple partners was so hot. She made me come over and she took my painfully hard cock out. It only took like 2 strokes and I came all over her boobs and tummy, which made her laugh.

She told me to go away, and we have never spoken of it. She never looked at me weird or anything, so I think she drunkenly forgot it. It’s been almost 30 years and I still think of that night when I jerk off or when I fuck my wife.

2
# 74066 - by JackieDaytona3019 / October 17, 2024
- Dreams and Wishes -
Bi-Sexual Male / 41

Wish I Was A Woman

Of all my sexual fantasies, the one I want the most is to be a woman for a day or a week or forever or whatever. I want to dress up girly and be hot and just be the biggest massive cock slut out there. But I don’t have the courage and I’m not slender enough or feminine enough to even think about trying.

2
# 74059 - by JackieDaytona3019 / October 17, 2024
- When I Was A Kid -
Bi-Sexual Male / 41

Me & Tim

When I was in like 1st or 2nd grade I had this friend Tim who was my age and he had a sister like 2 years older than him. So like 3rd-4th grade. I have older sisters too but they’re not relevant to this story.

For the life of me I don’t know how it started, but there’s a fence line near my house on the border of some school woods. Me and tim would go back there and get naked and touch each others dicks. We even got to the point where we used to suck each other, although I don’t think we have a really got hard.

His sister caught us on a sleepover at his house. She demanded we let her join in or she’d tell on us. So that night Tim and I got an up close look at a vagina and I got to watch a sister lick her brothers dick.

We did this once or twice more before his parents stopped allowing me to see them. I never got the full story, but I think it’s pretty obvious that they got caught exploring each other and they told them everything.

1
# 74058 - by JackieDaytona3019 / October 17, 2024
© Copyright 2026 Adult Confessions | All Rights Reserved.