True Sex Confessions With Pics @truesexconfessionswithpics - Tumblr Blog

Who said turning 50 would suck? When you're a multimillionaire, you can find a 20 year old ass like this that will do anything you ask.

My friend Kaylie was married at 19 to her high school sweet heart. They divorced at 26 after he cheated on her. She decided to start working out, get fake tits, tan a lot, and dress well. She lost 80 lbs from when she was married. She's now 28 and loving life. When her ex husband saw her new look and tried to get back with her, she obviously declined. But when he started to be an asshole about it, she said she would come over with a friend. He said sure. That friend was a trainer at her gym who was built like a Greek god. Her ex husband didn't really speak through the visit. Originally she only invited the trainer as a friend, but they've been an item ever since.

I'm a 6'11 personal trainer and athlete. I have a good body and dress well. I'd like to think my cock is more than proportional to my height. Sometimes shorter girls are curious about me but most women I date are at least 5'8. Many are gorgeous. But so many of the skinny ones can't handle me. I was getting bored with some of the women I was dating she a friend of mine told me about an escort his buddy had used who was very tall (most of her clients were extremely short and into being intimidated by her size). I looked her up. She's 6'6 with big fake tits and a round ass. She's also gorgeous. I decided to hire her - I'd never been with a woman over 6'2. I think she was surprised to find me as her client - though in the best possible way. I might have paid her for sex but she came twice while we fucked and didn't let me leave. She paid me back for another round. And then we basically ended up together, fucking all the time, intimidating all other couples around us with our height. And now she's pregnant with what will be a very tall baby.

You can’t see it here, but Jeannie is touching herself. She was an absolute nymphomaniac, and honestly needed to come ten times per day. We hooked up one night at a party and she liked that I came and then wanted to go right away with her again. I liked that she was so hot, had a killer ass, and wanted to fuck all the time. At first it was so exciting. We’d fuck in the car, and then again at the restaurant. She’d have her hand down my pants at a baseball game. She’d touch herself pretty much anywhere anytime and encouraged me to touch her. We fucked on the deck of a public pool (got caught obviously). At the beach she just wanted to fuck even without privacy. After a while of continuously getting caught, I was worried we’d actually get arrested. Plus I realized she was actually a really boring person and not interesting to talk to. She only wanted to talk about the previous and next time we were having sex. When I broke up with her, she was shocked, but was fucking a guy she met less than ten minutes later. My problem for a long time after that was that I wanted to go five or six times per day, and none of my subsequent girlfriends were interested in that. But at least the could have a conversation.

All my life I’ve always wanted to be with a busty girl. But just looking for a woman with huge tits isn’t exactly the way to find a partner. I met this girl on Tinder. She was super sweet and fun and beautiful, though I only saw close ups in her photos. And then we met. She wore loose fitting clothes so I couldn’t tell, but the date was going so well and when we kissed, I came close to her body and could tell that she was mostly boob up front. She was shy about them but I told her I loved big breasts. She showed them to me in my car on the first date. It was the greatest moment of my life. We have now been together for a year. She lives with me and I get to see her gigantic tits every day. She’s become more confident too, dressing to show off her insane cleavage. She even wore a bikini to the beach - she turned a lot of heads. She didn’t want me to show her face, but this picture gives you a pretty good idea of her curves.

Partied hard, picked this girl up last night even though I was so plastered. Woke up to find that incredible ass out the balcony. We were gonna get breakfast but got distracted...

My first wife always said I thought too much with my dick. She said I didn't deserve to have such a big one, since it sucked too much blood down there. She was probably right. She was my high school sweetheart and we married way too young. I had only fucked a few women before her. Ten years into our marriage, she wanted kids and I wanted to fuck women with gigantic tits. I'll admit that I slept with a lot of women while we were still married. I was very successful at work, and my wife was never very good at taking me. I ran a clothing import business and decided to bring in larger sized bras. I hired Jules, pictured, as our sales manager. She was terrible at it but she was also the reason my wife finally decided to leave me. Jules doesn't want marriage. She just wants to fuck me, be my arm candy, and that is perfect for me.

When you're 18 and taking a 25 year old woman who works mostly as an exotic dancer as your date to prom, she probably won't feel like wearing a gown. I had met her four months earlier and we had been having insane sex for about two weeks before I learned that she was a single mom of two and a dancer, and she learned I was still in high school. When that happened, we broke up for about three days only to get back together again. She was reluctant to come to my prom but I think she liked the attention. At least until we got caught fucking in the bathroom and had to leave...

When I broke my leg my neighbor told me his daughter might be able to drive me to work since she worked right near me. Let's just say my leg took an extra long time to heal...

Super cute new cashier at work. Flirted with her a bit and eventually we become friends on snapchat and Instagram. Quickly learn she has a very big boyfriend and no filter whatsoever. Sample posts: 'Luv when he comes 2 c me strait from the gym. I give him a Real work out!' 'Jake staid over again last nite. My parents weren't 2 happy mostly bc we kept waking up my bro LOL' 'Ugh so bored at work. Just wanna go to pound town ;P' 'Tried something new 4 Jakes bday but now I cant walk LOL gonna have 2 stay home 2day' 'Saw Jake flirting w some waitress. gonna have 2 show him why he's only mine ;)' 'LOL we got in trouble on the beach bc some1 saw us foolin around'

This is a picture from 8 years ago. I was dating the girl in the picture at the time. She was 19 years old in this picture. I was 32. We had been dating from basically the day after she turned 18. I would never in a million years have thought she was that young. She didn’t think I was that old. She was so sweet, and had unreal curves. Our fifth date was her senior prom. She wore this same dress. All eyes were on her, obviously. She wore this dress a lot because she only had a few that fit. And this was my favorite. We only lasted a couple years together because she became too consumed with college. But I still look back of this picture of her in this dress and wish I had her body again...

Where I work, it’s all women other than me. Young women. Fucking hot women. I’m an okay looking guy, but I’m also the only guy. Maybe as a result, the women seem to be very comfortable flaunting their bodies, as well as flirting with me. F, pictured here, sits right near me. This is more or less what she wears everyday. She isn’t even the most revealing woman on staff (that honor goes to a 30-something woman down the hall that dresses like a teenager). Without fail F always shows a lot of cleavage. She also flirts like hell with me - so do a few other women, but F gets most of my attention. For months, her tops would get more and more revealing, until she finally told me she had a huge crush on me, and insisted I go out with her. I didn’t complain. We lasted six months, and mostly ended when she decided to move jobs. While I’ve had some flings with other women in the office, none of them have the tits F did...

Yes, this is how my wife dresses to drop the kids off at school. Other parents stare and glare, but I can’t complain because at the end of the day, I come home to her.

This is my real estate agent. My wife couldn't understand why I insisted on seeing so many places, including those times she couldn't come...

My coworker insisted I would get along with her daughter. “We’re both single, after all”, she said. She told me her daughter was coming into town for the holidays, perhaps we could go to the mall together. I love my coworker, but I doubt that this is going to fly. Then I pick up her daughter. This is her daughter. 24, a fitness trainer (and self-professed attention whore). The first thing she tells me in the car is how she almost got caught masterbating on the plane. She tells me she actually needs to buy some things but then we can have some fun. And when she sees my blank stare, she says, don’t worry, we’re going to fuck. So I follow her around for what feels like forever - I snap a few pics of her for my friends. And then, sure enough, just when I think we’re going into another store, she brings me to the changerooms to try on some lingerie. And then she takes out my cock, sucks it, pops on a condom, and we’re fucking in the changeroom. Once I finish, she asks me to Christmas dinner. You can only imagine what happened that night...

I am a 43 year old man who has been described as George Clooney with a 6 pack. I’m 6′3, very fit and muscular, well hung, and extremely wealthy from working my ass off in my 20s. Now I basically spend my life looking for hot young things to fuck senseless. Not that I have to try very hard. If I’m not getting hit on by women, usually most of the girls I fuck want to come back for more.

Take, E, for example, the girl in this picture. She’s 20, a college sophomore, and in a loving relationship with a basketball player. But she calls me at least once per week to take care of her. Most of her friends are just as hot and sometimes they’ll call me too. E is particularly good at blowing me.

Some of my friends ask why I don’t settle with anyone. Then I show them pictures of E’s ass, or K’s tits, or the videos so many of these girls send me...

I’m a 24 year college football quarterback living in the Midwest. I’m over 6’4” and considered good looking so I’ve fucked countless women. But it’s rare that I fuck them more than once because, when the action starts, they are quite disappointed to find out how small my cock is. I’m barely 4.5” rock hard and pretty skinny. My middle finger is almost as thick.

But I somehow got this gorgeous girl to fall in love with me. She’s 21 and we moved in together about 18 months ago. Last weekend, she drunkenly confessed to an ongoing 2 year affair with our next door neighbor. Of course I quickly realized the reason she enthusiastically agreed to move in was to be closer to his huge cock. (I mean huge…KIK me at letstrythis1025 to see a picture). I got her to tell me every detail. She used to fuck him on my side of the bed all the time and he would wipe his huge cock on my pillow case after he came deep inside my precious girl. He forced her to degrade me while he was fucking her. He even made her call me several times with his cock in her mouth.

I absolutely devastated but I’ve jerked off to images of them together dozens of times already. What the hell is wrong me?

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