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Share stories, stories about being with older men especially. Mainly cause this just happened and I feel the need to post this and hopefully gain insight.
I (18) met an (46) older guy from cl. His pictures were sexy, being the handsome man he is. What intrigued me more was what he said; I could tell he's intelligent, kind, overall an interesting guy (masters in int'l business, banker all over the world. I already wrote the experience, separating it now because it's in first person.

I knocked on the door and he answered seconds after. "Hello, anon" I spoke in a bit of a rush due to nerves, I didn't realize I was pretty nervous. He, being a lovely host, got us waters. We sat on his couch, a half-floor below. We started talking, mainly he was asking me questions about me (school, family- we live in utah so people are usually interested in other's upbringings). He seemed to get a good impression of my personality, assuming I'm kind and such, I'm not a very prideful person though. I asked him if he came from here, and he followed by talking about his life. I don't interrupt as I'm more introverted and prefer to just listen without interruption.
Then he asks me about the specifics; "do you want to watch a movie first or go straight to it." I decided for the latter, which I kind of regret now. We go upstairs, start to slowly makeout (I would've preferred him to be a little more aggressive, no pain or anything, but loving with a sort of sense of urgency). He took off my clothes slowly and sucked me a little bit to get harder. For some reason it was hard to maintain an erection. Then I took off his clothes, we went on his bed continuing to make out. His body rubbing firmly against mine.
He was very respectful as well, but I really wanted his dick so I assured him of it. He fucked me for what felt like about 5 minutes and came. Then he tried getting me off, didn't really work after about 30 minutes. "This isn't working for me." I really don't know why this shit happens. I'm very sure I like older guys(now im questioning that), especially this guy, but this seems to happen.... he asked me how I got off, how often, with porn or not (obvs), made me realize I should cut back the fapping.

Or maybe diabetes affects sensory nerves more than I thought. Maybe I wasn't in the mood, come to think of it I wasn't horny the whole day but that's a lame excuse as far as I know.

Talking a little more, I took my turn to apologize, but he brushed it off saying I shouldn't be sorry for what I am. Kind of an insightful remark considering the situation nonetheless I'm really fucking worried about it still.. So I got dressed, we hugged and kissed and I left. He asked me earlier on in the emails if it would be regular, I said yes. Now after that experience, I'm anxiously pondering how he perceived me, if he was disappointed. I don't know, I just want this to continue, and I feel like I fucked up.

Do I even have a chance, do you think he would want to meet me again despite the mediocre (at best, for me... because... i didn't even orgasm) experience. I feel like I shouldn't care but I would really, really hate for this to ruin the now former possibilities.

I also made some minor yet dumb stoner mistakes too haha, a little embarrassed because he's pretty perceptive. he's liberal but raised mormon and put 'never' by drugs and i'm... yeah... so if he reads this lol oops shit. I kind of want to share a face pic of him but I just saw a Portuguese guy freak out on here. Although it's pretty obvious if you were to read this. Really obvious. it'd also be pretty weird if he read this.

the pic is related btw.
I know this gentleman . He's from SLUT. Didn't meet him personally (my fault we fell apart) but yeah, he definitely seemed someone with impressive personality. i say Girl....step up'yo game and stop flickering your bean befou you meet yo man. Trust me hunny .. men like these are rare, specially from the are. you know what i mean . Hold a nice convo and take another chance. Stop being a pussyboi . Now go SHAKE his WORLD girl . and yeah no face pics just like that . RESPECT darling RESPECT
Nice story. Cmon dude face pic. Or at least moar pics
>answer ad on craigslist
>older guy (mid 60's) looking to service
>arrange to meet him at his house
>get there. ring bell. he answers door
>he has a heavy german accent
>house is dimly lit
I'm gonna die
>go into kitchen. offers me a cup of coffee
>talk for 15 minutes
>he reaches over and gently puts his hand on mine
>finish coffee, he invites me into his bedroom
>strip down and make out on bed
>lube him up and fuck him for a few minutes
>he rolls me on my back and gives me a nice, slow, wet blow job
>I cum in his mouth
>he gets up, gets a warm wash cloth and towel and gently cleans my cock
>dress and have another cup of coffee with him

turns out he's been the manager of several high-end hotels and now does consulting in hospitality. very customer service oriented.
There's this guy in his early 60's that's contacted me on Grindr a couple times. We dirty talked a bit and talked about all these different fantasies and how he'd lay me down and give me a long, slow full body work over.

I'm outrageously horny and really tempted to go through with it, but I'm scared that I'll get there or I'll finish and just feel instant regret for getting busy with a dirty old man. Any advice?
Tell us more details. I wanna hear every little bit about this fuck session. What did you talk about? Any dirty talk?
International Business is a joke of a degree
A master's degree isn't a joke
>*I* already wrote the experience
>Separating it because it's in first person

What the hell do you think you were doing in the first para when you wrote "I" ?? First person? Second?

...sigh. And, I suppose that you've never thought that playtime with a guy around your age caused you instant regret, huh?

Just give it a try.
sure is mate
>Live in small village in middle of nowhere but surf cl anyway
>older guy pops up looking for inexperienced guys
>email tennis
>end up knocking on his door and my heart's beating a 1000 times a minute
>want to bail but he opens and I come in
>does not look like pictures
>he can tell I'm nervous
>suggests we start with a massage so I strip down and he goes at it
>feels really good but his house smells weird and I can't relax
>massages ass= instant boner
>keeps asking if I'm ok
>i turn over and he's hard and I instinctively start to suck him off
>grabs my hair and gets rough
>i moan like a bitch
>he gets more and more dominant
>cums in my mouth and makes me thank him
>make me cum in my hand and eat it

So went quite well but then he wanted to kiss on the way out and he had terrible breath so I didn't see him again
Well, I dunno. This might sound vain but I would literally die if anybody found out about that kind of thing. I guess I'm just really awkward in that regard. It'd be my first time, too.
> ad on craigslist
> attractive retarded guy lives in trailer on disability
> go to his room
> 69, ride him a little, he gives me a blow job.
> I come he doesn't
why am I a failure at everything.
>Be me 22 lame Virgin because average self hating gay
>Move OS for a bit and discover Grindr just before I leave
>Crashing at family's in the city check Grindr and get a message from a guy not far away who wants to fuck
>Decide fuck it I just need to know what its like
>Get to the public bathroom where he said to meet (cliche and gross I know)
>Turns out he's really large, like not sure how he got through the door
>Think fuck its too late now
>Suck him a little to get him hard, he fucks me for like maybe 2 mins
>He cums pulls up pants and leaves
>I just sit there for a minute disgusted at myself
>Still am a little to this day
Hey, I'm a 22yo sissy and I'm looking for someone to talk dirty to me on the phone....any takers? Please send me numbers!
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I love wearing girls panties. I get so hard.
OP your writing was so atrocious I could barely follow your story. Cut back on the pot
Help me figure out what the hell happened to me. This was last week.

>browsing craigslist all weekend
>see ad from big muscle daddy who wants young inexperienced tops
> I can never find muscle daddies, only fat old men. Plus I've always wanted to top so this seems like a prime opportunity
> answer ad and immediately receive address and "rules"
>starting to think this is weird, but mad horny so I drive over
> buzz in and ride elevator upstairs
> door is open, creepy smelly man greets me and walks me to bed with daddy face down with mask on
> only has a hole for mouth
> glorious bubble butt and big strong shoulders and arms
> hairy forearms and legs fuckyeah.jpg
> there is a black kid and an asian kid there, so ok im in a gangbang
> climb ontop of daddy and grind my dick into his ass to get hard
> put on condom, smelly man says hes clean, but still
> start fucking his abused ass (im quite ashamed but was so horny)
> apparently hes a cop with wife and kid whose freshman in college
> fuck him for a bit then pull out and cum onto his ass
> push my load into his hole with my

Theres more if theres interest. Was such a surreal experience. Not sure if i raped a cop, fucked a prostitute, or if I will find myself on the internet someday, but it will be worth it after i test negative for stds.

I like to get off to the fact that there may be a hot muscle bear cop whos wife and kids have no idea he likes to get fucked and used anonymously by a bunch of random young strangers and takes their loads up his ass.
+1 :O

Of course you do. A Daddy would never get rid of fresh meat he enjoyed playing with.
Any pics of him?
This is the single gayest post I have ever read on this board.
kill you'reself :^)
*yourself :^)
What does this mean?

I have a chest pic on my comp I can post like tmo
> be me, alone, freshman
> email tennis this older guy all Summer
> his pics are hot
> finally hook up
> I go to his house at 11pm
> he's older than expected, v. Fit ( a little too fit for my liking)
> no ass.
> talk a lot, he showers, talk etc.
> we go to his bedroom, kiss and stroke etc.
> he fingers me, I blow his 7inchish cock
> Fucks me properly in every position, I'm moaning uncontrollably
> pulls out after 10 mins
> I ask if he came
> nope.
> he gives me A++ massage
> finger fucks me and wanks me off
> I shower and leave. He hasn't come.

He was a beastly fucksman but he was a bit too rough with his hands. Also he kept sucking my balls too hard. Thought they were gonna come off. I'll go back to him if I can't find a better buddy.
Bump this shit
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Underrated post. I like you, here's my dick.
post it either way!
Okay guys, so I've never hooked up (or slept) with a guy before and I really need some advice on what to do with the following;

>58 year old guy on Grindr contacts me
>He's actually pretty sexy, good dick, nice body
>Chat for a bit, talk about our kinks
>He wants to meet up
>Very polite and respectful, says I call the shots and he'll offer absolute discretion
>Says we can either meet in public first or at his house while his wife is away
>I can go over on Tuesday or I have to wait a few weeks while he's out of the country

Does anyone have any advice? I wanna do it, but I'm pants-shittingly nervous about the entire thing. I've never exposed myself to someone else and I'm pretty insecure. Just some tips or a nice anecdote or some shit would be appreciated
Contacted a guy on grindr today (one of the "newcomers", although I live in an area where 30km can be as close as 30km... or past a leg of water and a 2h drive.
So, we started exchanging pics through grindr (which is shit unless you've loaded them first).
Hours later we were still chatting on grindr/whatsapp, I then want to speak to him to hear his "funny accent" (scottish, which turns me on).
Several videos/more pics later, horny as fuck. Call him, end up coming on video and swap videos. Logistics are a bit difficult, but he'll be taking a day off "sometime" soon so that we can meet (I work shifts and evenings are usually shit for me, so daytime is best).
10/10 horny.
Go for it anon.
If you don't like it, you can always tell him and go.
um. excuse me sir. im gonna have to suck that for you.
You again from /lgbt/. Post his pic, crop his head if you have to.

My two cents, since you're really looking for advice.

Online hookups can always be sketchy, but you're an adult and you can make your own decisions. There are lots of people (myself included) who utilize and enjoy things like Grindr, A4A, Daddyhunt, and Craigslist on a regular basis and have had successful, non-shitty, fun times.

On the flipside, there is always the possibility for shitty times: guy lied about his age, weight, status, etc. It happens but there are lots of ways to prevent these situations.

> Agree to meet in public first
Go out for coffee. Talk to him first in a safe, bright, public space. Use this opportunity to make sure he isn't a creep, and to settle and last second regrets before D's pop out.

> Tell a friend where you're going
Provide another safety net for yourself by letting a friend know that you're going on a date/hookup whatever, the address you're going to, and to call you in X hours if you don't check in afterwards.

> Bring your own shit
Always have condoms and lube so that there's no excuse to play safely.

Honestly if you have these three things in order you will 99% have a fun, safe time. The fact that he's agreed to put you in charge is already a good sign but again, to put your mind at ease, you can always meet up first and see if he's a freak or not.

Online stuff like Grindr is for short circuiting the pageantry of traditional dating and getting straight to the point; if it makes you nervous, then don't do it. If you accept the potential risks but can make smart sensible choices, then get your boipussy wet and enjoy life. Just make adult decisions about your life.
Now that I wrote all that shit out, reward me with pics
What he said, but
>Always have condoms and lube so that there's no excuse NOT to play safely

Grindr is great because it's for sex. People go there to fuck and get their sex fix. Sometimes great things happen, sometimes they don't. Make sure you've got the right cards by following ^'s advice and keep your brain over your shoulders and not on your dick.
You have kik?
I spent 4 years as a high-end escort/sugar baby. Most of my "suitors" were older gentlemen, all of them wealthy.

I took a sort of "Companion" approach and only worked with clients who I vetted and found good enough to be with. Sex was never promised, but I love older men in Italian suits staying in luxury hotel suites, so I probably ended up sleeping with 65-70% of them. Quite a few just wanted companionship. Some paid me as a travel companion, so I was whisked off to Italy, France, Maldives, and India where we had amazing food and fucked like rabbits on scenic verandas and in private pools.

My specialty was dealing with lonely men who needed companionship. Some wanted a drinking buddy, some would pay for 10 hours just so I could come "home" at night and kiss them goodbye on their way to work. I was a well-educated societal fashion accessory. All the concierges and bartenders at the top local hotels knew me and got a kickback for recommending a client to me. After 4 years, I was charging $350 an hour and had two "boyfriends" — one who paid for my apartment, one who gave me $5000 a month allowance.

If you want advice on how to deal with older men whether it's serious dating, a CL hookup, or you're escorting, here are a few pointers:

1. They're terrified of being with a younger man more than you're terrified of being with an older one. They don't know how to entertain you, they're worried about subconsciously "parenting" you. Even if you want them to dominate you, you'll have to take charge at first. Let them know you're not a fragile child. Let them know you don't need keys jangled in your face to keep you entertained. If you make the suggestions, they'll feel a lot more comfortable.
2. Older men aren't necessarily more experienced. Give feedback, take things slow. No one's a sex expert.
3. Let them feel superior. Don't try to outsmart them, don't argue about things you don't know about. Listen. They'll respect you a lot more and respect's a big turn-on.
try again bro. Happens to me every once in a while (not being able to cum). it happens when you bottom. You'll get there soon, i promise

also, where did u see a portuguese guy freak out? cuz i'm portuguese and kinda curious now
Too jealous.
Thanks for all the advice, I didn't think about the friend system. I think I'm gonna do it. Will report back if I do.

How did you get into the business?
Honestly, I saw a market for it and went for it. I actually sort of hate sex, so it's not like I was "selling myself" anymore than when I was doing marketing at ING. I started with Grindr. I also frequented luxury hotel bars on weekdays, drinking a martini at the bar alone and chatting up businessmen and getting to know the staff. The people there were almost exclusively people traveling on business, so I got one or two johns, but mostly I learned about their lives, what a day in the life looks like for them, and made friends with a few of them. I discovered that a lot of these guys really just wanted a friend to have dinner with, bounce ideas off of, and hit up the Indian casino in their rented sports car and play blackjack. It helped that I'm really good at blackjack. And knew a thing or two about cars (but not too much that they couldn't feel superior and teach me).

With this knowledge, I actually got a pretty good repeat business of straight men who liked having a gay wingman who could hold his liquor, chat up strippers (and attract them all to our table — pink champagne is cheap whore fly paper), beat him at cards, and have a good knowledge of the local hotspots. For a good two years, half my clientele was straight men recommended by the bartender. "If you need a local guide, that guy with the martini once got my friend a threesome with strippers. Well worth the money. And I can get you guys into a strip club for free if you show them this..."

Escorting gets a bad rap for being a fancy word for prostitution, but if you're good looking, dress well, well-educated, are professional, and EAT SOMETHING BEFORE YOU DRINK (learned this one the hard way), sex is almost always the last thing on a man's mind.

By the way — Über revolutionized escorting. Cheap, on-demand towncars!
Only if I can suck a nice one too
why would you bump this
In some fields it is. Like education, you won't get paid anymore than someone with a bachelor's in most states, so it's a waste.
>while his wifes away
don't do it.
that is sick and cruel.
Here's a story I wrote. I've never posted it anywhere before.
Tell me what you think!

(I'm posting it here because it would NEVER pass the content guidelines on Nifty!)
you are garbage, the reason i dont "date" anymore. i cant trust anyone because the shit ass guys like that
Sounds like something a virgin would write. Also

>sniffing a childs underwear
Absolutely fucking vile
Fukien hot Ty
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Very poorly written. Indeed no site should ever accept that
>Be me 9 years old
>have a best friend
>we literally do everything together
>best friend lives with his father who is a 30 years old HUNK
>used to spend a lot of time in his house and his dad acted strange around me
>one day coming home from school
>it is raining like a motherfucker
>reach front door realise that I forgot my keys in the morning
>knock on door then realise that my parents are at work
>im wet and cold
>decide that im going to go to my friend's house which is not far away
>5 mins later im infront of his house
>knock on door
>his father answers
>he immediately knows what happened because this was not the first time that i forget my keys
>invites me in
>sees that im wet and cold

Nah, don't bother.
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> 9 year old shota
> 30 year old "daddy"

No thanks. I don't want to hear about a shota and a guy nearly my age.
This thread is shit
Post son greentexts
Yes please.
>Be 19. Go to meet a 46 year old muscle daddy, hairy in all the right ways
>Get there. He says he's with his nephew.
>See proof. ACTUAL Nephew.
>They both fuck me from both ends
>BB but don't care.
>Becomes a regular thing
>Eventually nephew moves away and uncle get a BF
>I become their regular third
posted in another thread but here goes

>exchange contact info with a guy from a gay thread
>talking, same interests, swap pics, like what we see
>talking every day for months, sexting
>assume roles of sissy sub, get right into it
>invites me down for a few weeks
>why not
>order sex clothing/items
>summer approaches
>get on train, meet him at station
>lets me get settled, shows me around town, buys me a meal and a few drinks, head back to his
>get right into it, get dressed like a sissy slut in his bathroom, all over each other
>fucks me all over his apartment
>have filthy kinky sex every day
>invites another guy to join in
>spit roasted
>love it
>end up spending the whole summer as his filthy slave
>hot passionate sex on the last night
>kisses me goodbye the next morning and pays for my train ticket home
>occasionally talk to him and game with him when we have the time
Just finish the story
op here,
the man I met is supposedly reconciling with his ex. oh well. Quite a charmer he was but not the most genuine guy I've met.
sorry to hear that bro
You're pretty good at this. You said "if it makes you nervous, then don't do it" so what alternatives are there? I'm desperate to get wild but I freak out whenever I come close to discussing meets on Grindr
thanks man. Made it seem like he was interested to know me, almost like we could be good friends. nope.avi
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Guy who wrote that out here. Let's back it up a bit. As I mentioned, hookup apps/sites like Grindr put you in an interesting situation because it fast tracks sex. Why is that scary? You're putting yourself in a vulnerable position (pun intended) before, in most cases, you even get to KNOW the guy. We're talking about taking off clothes, being alone for X amount of time, and being very exposed with complete and total strangers. Literally anything can happen, and that is justifiably scary on paper.

However, people do take these risks with all the proper precautions I mentioned and have a great time. One thing to keep in mind is that to them, you're a stranger too. Any sane human being would want to make sure that they feel just as safe as you do in an anonymous hookup. Use the opportunity before a meeting to figure out if this is the case and bail if it isn't. Use the shroud of meeting in a public place with tons of people around to make an undisputed exit if you need to make one. Don't put yourself in a position where you want to say "no" but you're in his house and in the middle of buttfuck nowhere.

Now, alternatives. The anonymous hookup thing is still too scary for you - do it the old fashioned way. Go out, find the local gay neighborhoods and hangouts. Talk to people at coffee shops, gyms, and bars. Find a path to sex built on real human interaction and connection, not websites. Grindr is great at providing dong on the go, but oftentimes puts people in a "meat market" mentality that makes it easy to forget that there are people at the end of those ass pics. Foster a sense of familiarity with the guys that really interest you, and you won't have to worry about being vulnerable - physically or emotionally - in front of them.

> Grindr is for fast sex, the bold, the smart
> But don't be afraid to meet people the old fashioned (and honestly, better) way
> You still didn't give pics, you little fuccboi
I wasn't the guy you just responded to but I was the original one you wrote the post for. Thanks for all the advice. I decided to abstain from meeting the dude though, he turned out to be really pushy and kind of an arsehole and the more I think about it the less cool I am with sleeping with a married guy.

If I remember when I get home I'll put up his dick pics.
Well there you go. Just remember, if even 1% of it seems sketchy don't be afraid to back off. You don't owe that guy shit, and there's always the next dude in line. Never feel like you have to settle or do something to make someone happy/prevent them from getting mad.
it's really fucking upsetting when they don't come.

makes me feel like shit, like "oh - I enjoyed myself but clearly he didn't enjoy me :\"
>Tell us more details. I wanna hear every little bit about this fuck session. What did you talk about? Any dirty talk?

Not much more to say. We got on the bed and started making out and then went down on each other. It was all very "sweet" for lack of a better world.

When I was fucking him he was grunting quietly and he was tight. I was surprised I didn't get off by fucking him.
>Sounds like something a virgin would write.
>Screaming inches from a drunk's face doesn't wake him.
Make that someone who hasn't even been drunk before.
i never been in a relationship but i met this hot buff guy at a halloween festival. hes really nice and like 2 times bigger and older than me.hes really nice but lives really far,he invited me to stay at his house for a weekend if i made the trip over theree im kind of scared of stds or getting murdered. but hes really hot.am i just being paranoid?
I honestly wouldn't worry too much about murder. If someone wanted to murder you, they wouldn't give you an invite first.

Two bits of advice: STD's can be avoided by using protection. Murder can take you by surprise, but be sure to let people know where you're going. Mention it on Facebook, tell your friend. Text that friend the address and tell him the name of the man you're staying with. And then casually let the man know that your friends know where you are.

If you're too embarrassed or ashamed to tell anyone where you're going, perhaps you should reconsider your motivation for going.
Told this story before. On phone so no greentext.

Answered an ad on craigslist from a guy in his mid-50's looking for a younger guy (i'm early 20's). He's divorced, has the house. Two kids at college about an hour away so no interruptions.

Start meeting up with him at his house. He's gray hair, decent shape, about 7 inch cock and average girth. Total top which was good because i'm a total bottom.

When we would have sex it was always in his daughters bedroom. He said it was more comfortable in there. One night we had just finished and we were just laying there. I liked to play with his cock after sex keeping it semi since I liked how it flopped on his thigh. He asked what my fantasies were and I really didn't have much to say. Then I asked him.

He said he hoped I would not be skeeved out but he always fantasized about having sex with his daughter. He insisted he would never do that but sometimes when we had sex he imagined I was his daughter. He also confessed that the reason we used her bed was because he could smell her in there.

I could tell it turned him on because he got hard again and fucked me passionately after we talked.

About a week later his daughter came home for the weekend and left some of her clothes there for him to wash. When I came over he asked if I'd wear her panties when we had sex. I was not sure about it but he insisted so I said ok. When we were done he said fucking me doggy with me wearing her panties was great.

I came over a couple of days later and he asked if I'd do him a favor. He said he hadn't washed her clothes and asked if I'd take some of them and wear them when we had sex. I said ok and when he brought me into her bedroom he had already laid out what he wanted me to wear. Panties, bra, short skirt and a blouse. I got dressed and we started making out on the bed and eventually he rolled me on my stomach, lifted the skirt and fucked me hard. I found it weird but exciting.

After that I had to dress whenever I came over.
Am i the only one around here who finds this somewhat wrong?
I mean seriously, paying for companionship? How lonely are these people?
I hope at the very least, Anon did something good to them, minus the sex.
I'd rather be alone than be in a fake relationship where I pay for sex, but there's nothing too WRONG about it. Both guys are consenting adults that are giving their end of the deal (money for sex+fun time). I also worry about the guys who escort, since that seems like a gig that would eventually dry up when you get older. Not so bad if you actually anticipate it and try to transition into an actual job or something, but if not, the gay death could be especially painful here.

There's always a trade-off in these relationships. I'm an older guy and like younger guys (fuck your judgments). I've met younger guys into older guys and we've had a pretty decent sexual relationship. But (a) if they are students I insist they keep up with their school work, (b) help them set goals, (c) insist they have a job and (d) not depend on me for finances. Do I make sure they are comfortable? Sure. I don't want them to feel they need to spend 40 hours at school and another 40 hours working to support themselves so I can provide a place to live and food to eat. Do I expect them to be sexually available? Yes, but it's not one-sided.

The relationship lasts as long as it can and eventually after graduation they can move on with their lives. Until then it's fun.

As I said, fuck your judgments.
I think for a lot of them, spending $2000 on a great night with a person withholding judgement, wanting more from them than just business expertise or professionalism, and having a pretty face to look at and hold was much better spent than going on some vacation alone or entertaining people who were fake and competitive.

I realize, of course, that you could say *I* was fake, but I found the key to a great escort is to be yourself, just more patient and more flirtatious. I genuinely enjoyed spending time with these men, and they genuinely enjoyed spending time with me. But if the man was a jerk, I called him out on it. Sometimes they wanted to treat me like a hooker and I reminded them that I was a person too. Most of the time, they recognized this and had more fun. The other times, I told them that if they wanted a whore, they should have picked one up off the street; I forwent any payment, and left.

How lonely were they? They ranged from very lonely to just needing a friend. I'd hardly say I'm lonely, but I certainly would appreciate a friendly companion when I work hard and travel all the time.

All said, you're not wrong. But I was exceedingly good to them, and they were usually exceedingly good in return.

I escorted until I was 28 and my years spent learning what to say, how to say it, and when allowed me to get a good job immediately afterwards. And a few of the men I met were more than happy to offer me jobs up my alley.

Good on you, Anon. I've known a few sugar babies and they found that having the structured and regimented life a sugar daddy requires helped them get their life on track, took their worries off finances, and they had fun in the meantime. My daddies were some of the best men I've known.
Ive had 2 experiences with older guys, both were 3 months ago 2 weeks apart. First time I had posted a CL add looking for young black guys (Bi here, only 1 of the 5 guys ive hooked up with wasn't black.. kinda a fiend for black cock and ass) no hits on anything then a 45 year old black guy with a wife and kids emailed me. I didnt plan on responding but I hadnt found anyone else and I was soo horny, end up emailing for a bit, then we txted for a while, ended up meeting up at a walmart parking lot to talk before going back to my place. we talked in his car for about 5 minutes, he was fairly charming and for a older guy he was in amazing shape. we ended up going back to my place, smoked a blunt, made out for like 15 minutes then he slowly started working his fingers into my ass. I had never bottomed so this kinda was not ok with me at first but he was kissing me so deep and his huge 9 inch black cockfelt so amazing grinding up against me. he ends up getting on top of me and starts kissing me down my body til he got to my dick, he sucked me off for a bit, then rimmed my ass. I was pretty much in fucking ecstasy at that point, none of the guys i had been with prior had any experience compared to this guy and then I felt him start lubing up my ass, looked down to see his beautiful cock wrapped in a condom and within another minute or so he was fucking me missionary. it hurt soo fucking bad but he was kissing me the entire time and holding my arms to the bed so i really couldnt do much and after a few minutes the pain stopped and turned into incredible pleasure. he ended up fucking me for about 15 minutes, the last 5 pretty rough doggystyle before he blew a giant load in the condom inside me (at the time I didn't give a fuck it was the best sex i had with a guy and still is by far) after he busted he pulled out, the condom had sooo much fucking cum in it i was shocked, then he sucked my dick til I came. After I came he left. I miss him honestly.

Is pic related? I'm meeting a guy tomorrow night who says he has a 9" cock. I've met him a couple of times but just for coffee. Never seen a real cock in person that was over 6.5" so curious about it.
That's gross.
Yea thats a pic of his dick, honestly theres nothing wrong with a 5-7 in my opinion, and to be honest giving him head was awful I pretty much felt like i was choking the whole time, hurt like hell when he got it in me, but it seriously was fucking amazing once I got used to it. Idk if you plan on bottoming for the guy but if you do make sure he goes at your pace, if he starts pounding you with a cock that big itll pretty much ruin your day.
OP is that your pic? It's super hot.
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Hooked up with a married daddy from adam4adam.com. I went over to his house on a morning he didnt have to work and his wife wasnt home. He leaves the the glass patio door going into his basement unlocked as was planned. Go inside and see him playing with his hard massive cock. I swear it was 9" long and really thick. I get a closer look at the guys face and realize it'a my old swim team coach. I get scared he would recognize me. Luckily he didn't and he motions me over. I go over and he gets up and grabs me and puts me on my knees. He then grabs his big thick cock and tells me to open my mouth. I do as told and he starts slowly sticking it in my mouth. Teasing me with it. I'm hard as fuck now and I start going to town on it.

He starts going deeper in my throat nearly choking me. He then pullee back and let me take control. I sucked his dick for a good hour. I didn't want to stop. He finally couldn't hold it in and shot a massive load all over my face. I clean up and left.

Best cock i have ever sucked. I have his email and have been thinking about his cock a lot since then. Gonna reach out to him soon. Pic is of him.
The pic is of Wyatt from Chaosmen
What's his acct name? Face pics?
>be 30
>constantly sucked my own cock as a skinny teen
>after growing up, couldn't do it anymore and started to miss it
>sexually active as a straight man for 13 years, rarely single
>really craving a cock in my mouth
>start posting on craigslist and reading posts, spend weeks trying to find a chill, clean guy
>meet a bi military guy in his mid 20s, beautiful cock
>we talk for a while, trust each other, trade face pics
> go to his place and he senses I'm super nervous and so we just hang out
>he pulls out his ipad and starts browsing porn, I can see his cock getting hard in his gym shorts
>can't stop staring at it
>he asks if it's ok if he strokes it a little and I happily agree
>see the first hard cock that's not my own, get very excited
>ask if I can stroke it and he says yes, feels so good in my hands
>lick the head and slip it into my mouth, then my instincts kick in and I start sucking it
>he moans and tells me it feels incredible
>I get such a rush and hungrily suck and lick it
>he tells me he's getting close and I double my efforts
>he tells me he's coming and I moan as he shoots his hot load in my mouth
>swallow eagerly as I continue sucking him
>so good
>tells me its the best head he's ever had, from a guy or girl
>meet up again in a few days and a few times after that and I keep sucking him off
>enjoy it so much, but he moves for work shortly after that
>can't find another guy in my area that's not a total old creep or doesn't think 30 is too old
>I miss it so much already

So hot! Sexy chest and cock!

Share stories after you bottom for him!
>he moves for work shortly after that

Do you guys still keep in touch? Did you become friends? I want you two to be bf and bf.
We did for a while and started to become friends. He would send me really hot pics of his hard cock and I would tell him about what I'd like to do with it.

Then he saw a picture of me with an ex-gf and became obsessed with wanting nude pics of her. I don't share other people's nudes, so I said no. He asked for her contact info and I said no. Every time we talked he brought her up, wanted me to tell him stories about having sex with her while he jerked off. I got tired of it.
Wtf that took a really weird, shitty turn. Maybe he got obsessed with her cause of her connection to you? I dont get it. Sorry anon.
Nah, I think it's because he's bi and she's really hot. He had nothing nice to say about his former girlfriends and their appearances.

He seemed like a really cool guy. He was decent-looking, clean, and sexually laid-back. After getting to know him, I think his personality is a tad lacking. Still, I'd totally suck his dick again if he were back lol

If I can find another good-looking guy in my area with a nice cock who isn't a total creep, I'd happily move on.
I started going to school in New York when I was 19, and quickly discovered the joys of online hookups. I’m pretty boring and vanilla usually, but one day I ran across an ad from an older man. He wanted to buy used cum-rags from younger guys: tissues, towels, toilet paper, whatever.

I’ve never given or received money for sex, and I replied to the ad more out of curiosity and amusement than a need for money. He offered $10 per load, and I didn’t haggle. I saved up all my cum tissues for the next six days, then contacted him again to set up a meeting.

We met in a Starbucks in Manhattan, midday on a Saturday. It was pretty crowded. I took a seat at the countertop in front of the window, and waited for him to text or show up. I’d brought eight used tissues with me, including a fresh wet one that I’d “prepared” just before leaving home.
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In walks a flabby middle-aged pale white dude, kind of moon-faced and clean-shaven (think Lutz from 30 Rock, but about 10 years older). He couldn’t have been more conspicuous if he tried. He probably was trying. He was wearing a black trench coat, black sunglasses, and a baseball cap. He spotted me in the window (I’d told him what I was wearing, we never exchanged pics), walked in, and took a seat next to me.

Even his behavior seemed ridiculously suspicious and conspicuous (I was a bit nervous and paranoid about the whole bizarre situation). He stared forward, never looked at me, and asked (a bit too loudly) “Do you have the merchandise?” He was acting like a fucking Spy vs. Spy cartoon. I opened my backpack, took out the Ziploc, and passed it to him under the table, as sneakily and discreetly as I could.

As it turned out, discretion was not a part of his plan. He took the Ziploc from me, opened it up, and dumped all the tissues out onto the countertop. At that point, my flight instincts kicked in, I didn’t even care about the money, so I immediately started getting out of my chair. He caught my shoulder and pushed me back into my seat. Again, too loudly, he said “Look at me.”

One by one, he stuffed all eight jizz-encrusted tissues into his mouth, holding eye contact the whole time. I was pretty much frozen in place. He didn’t chew, he didn’t swallow, he just filled his mouth with jizz-paper and held it there. It was ridiculous, his cheeks were bulging out and everything. He pulled out his wallet, counted out eighty dollars, then got up and walked out the door with a mouth full of tissue paper. I took my money and got the fuck out of there.

And that was pretty much it, the strangest sexual encounter of my life. He emailed me before I even got home, thanking me for “quality merchandise,” and told me to contact him if I ever wanted to “set up another transaction.” I did not reply.
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Did it ever occur to you that was part of his fantasy?
Wtf are you even asking? What dumbass WOULDNT think that?
Alright, here's my most recent, and best

>be 22
>head out to city on a friday
>wind up in a bathhouse
>Blackout fridays
>shower and steam
>while I'm steaming, porn is playing opposite me
>start playing with my dick to get hard
>guy next to me notices and goes to suck me
>sucks for a little while, then I offer
>decent size, about 6", nice looking
>suck him on my knees under the porn screen
>lasts a few minutes and gathers a crowd
>guy cums in my mouth
>went to hold it in till I could get to the shower and spit
>go to leave, another guy grabs my wrist
>Nordic god, must be in his 30's, sort blonde hair, shaved, muscled, tanned, cock at least 7"
>gently pulls me down between his legs
>start sucking him off with gusto
>his friend is sitting next to him watching me and they make light, casual conversation like I'm not even there
>after a while my knees start to get sore and I feel like I'm not gonna finish him so I get up to leave
>head to the spa
>Sitting down in the spa is a bunch of older guys, mid 50's and up
>Not into that much older, so I'm just chilling for a bit when I feel hands on my back
>Nordic god followed me
>Sits behind me and pulls me into his lap
>starts lightly grinding his cock against my rosebud in front of this group of old men
>an old man goes to touch me, but nordic god gives him a look like "he's mine" and he backs off
>inserts a finger, then two
>I'm getting stretched and fingered under the water of this spa
>few minutes I'm stretched enough
>pulls me out and leads me upstairs
>blackout area
>walk through the darkness until we find a room he'd been looking for
>go through, it's a giant padded floor
>close the door and now I can't see anything
>gently pushes me to the floor and tells me to get on my knees since he knows I want to be dominated
>follow orders and feel his dick start grinding up against me
>finally he pushes in
>It hurts, since this is the first time I'd had sex in a while, and I just realised he hadn't used a condom
>he pushes me down so my dick is rubbing against the padded floor
>I'd lubed beforehand so it felt really good
>start fucking frog-style, pushing me into the floor
>Only takes a couple of minutes before he blows inside me
>I can feel the creampie dripping onto my balls
>cum into the floor, exhausted
>starts giving me a nice massage after he pulls out, which I really needed
>apologizes for going bareback, since it wasn't usually his thing but he couldn't resist this time and assures me he's clean
>we make small talk and he hopes I enjoy the rest of my night
I didn't do much else that night after him, since it just wasn't as good.
There was this guy, ill call him G. G had flirted with me all year, and i was kind of out as bi to everyone in the school. We fooled around, kissed a few times during the year, but at the graduation party we were around a small fire the entire time, and it got to the point where we stumbled drunk to my car and to the back seat. We got in the back seat and waited for the car light to turn off before ripping eachothers clothes off. I got his cock in my hand and spit on it, slowly jacking it off a bit. I then got it into my mouth and started bobbing up and down and letting it hit the back of my mouth and into my throat. He reached around and started to finger me pretty well, getting two fingers up my ass. He started whispering in my ear, which is a massive turn on, and in this time had got a condom on. He began to push it into my ass, which hurt a ton. he fucked me doggy style, missionary, and i rode him. He was about to cum so i pulled off the condom and swallowed a massive load. I sucked his cock once more that night and we spend the night in my car. my asshole was still sore the next day.
more like this gif
face pic or that shit never happened. c'mon op
you're over thinking things. if anything he wants it to be regular so he has a young ass to plow
This sounds like the opening narration of a gay Wes Anderson movie.
Been asked to meet an older guy tomorrow, 44, very athletic, nicely hung, went to Oxford and simply wants to go for a coffee.

Never met someone using the internet before, so I'm undecided even though it's super tempting.

Anyone have advice?
I'm 18yo and this 42yo guy (according to his profile at least) contacts me on scruff
Should I do it?

(i may also be a virgin, not that I give a crap about losing your virginity to someone special or whatever)
Fucking fund it.

>Bill Murray as the sugar daddy
When I was 19, I had a 2-year relationship with a 55-year old guy. He was a rich art dealer here in Amsterdam, and eventually I moved in with him. He was really kinky. He loved the CMNM dynamic, so I always had to be nude when I was alone with him. He also liked to fuck me and cum inside before every public event we had to go to, so that he knew I was walking around with cum in my ass the whole time He even arranged to do a nude 'art' photoshoot with me, in which I sucked his dick while a photographer took pictures.
Elaborate more on the sex rather than just "sex happened"
Don't feel like you have to do anything.
2 years ago when I was 20 I saw my AP history teacher out at the bar. I knew he was gay so I figured I would just say hi. He chatted for a while, and I realized he didn't know who I was because I looked so different from high school. Anyways he said it was great to see me, the usual stuff, but then asked if I liked to swim. I told him I did and he said "oh great take my number and you can come over for a swim in my pool tonight" biggest fucking curveball of my life. He was a bigger guy, bald, but very fit with huge biceps. He told me he was 35 but I later learned he was 39. Anyways fast forward to that night it's 2 am I go to his place and we swim. He decides to swim in his underwear. He says he's cold and says we should dry off inside. Then inside he tells me he loves to give massages. I lay on my stomach and instantly get a raging hard on from feeling how strong he is. Anyways he flips me over an giggles at my boner and asks if he can touch it. Anyways we have this amazing time where he rims me for almost 45 minutes we we blow each other and make out for like three hours. Anyways he was no the principal of he town next to my high school, and some how very wealthy. For about the next two years he would take me shopping buying me whatever I wanted, pay a bunch of my bills, ect. Probably the craziest thing to ever happen in my life ever.
>>he hadn't used a condom
use protection you fucking retard
Pics pls
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