Gutsiest pickup attempt

  • ChicagoSteve

    Posts: 1279

    Feb 19, 2015 1:56 AM GMT
    This was several years ago, but I was on a Chicago commuter train coming back into the city. I saw a very cute young guy and I was thinking of a way to get his attention. I walked up to his seat and asked him if he had a pen I could borrow. I went back to my seat and wrote a note asking if I could buy him a drink and included my number. I then went back to where he was sitting and gave him his pen back, along with the note. When he was reading it he cracked the biggest smile. He never called, but at least I tried. I gave myself credit on that one. I've never done anything like that before or since.

    Would be interested in hearing stories from other guys.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 19, 2015 2:52 AM GMT
    This was also a number of years ago. I pulled into a commuter lot after work one hot summer evening to change into a T-shirt and shorts in the car before going out. I parked between two cars and took off my dress shirt and pants and was reaching for my shorts when I realized there was a state cop in an unmarked cop car on the passenger side. He was staring intently at me. I was so startled I jumped and my knee hit the steering wheel. Our eyes met and he smiled at me and made a little twitch with his eyebrows. I pulled on my shorts and then looked over and he was still staring at me. So I rolled down the window and he did the same. I said "I guess I put on a show for you." He said, "Yes you did." So throwing all caution to the wind I said "Did you like it?". He gave me a big smile and said, " Yes I did." I was really surprised by how this was going and kind of lost my cool and actually didn't know what to say then, lol. He took out a pen, wrote something on a piece of paper and handed it to me - it was his number. Then he started up the car, said "Call me", and pulled out. Definitely glad I made that stop!
  • Posted by a hidden member.
    Log in to view his profile

    Feb 19, 2015 5:45 AM GMT
    Last summer I was in footlocker looking at shoes (im a nike freerun addict) and a guy who was very charismatic approached me and asked if I wrestled I was like no I just am into lifting, he was like well you look great and then we got on the whole lifting thing and how I want to compete and how I used to be the fat kid blah blah blah... I kinda got the hint that he was trying to pick me up but I wasn't sure and then after I got my shoes we walked out of the store and I was like well have a good day, and he was like you to I'm sorry for wasting your time. At the time I was really confused because I never really had anyone try and pick me up plus I wasn't out yet. Looking back I wish I would have asked if he was gay or if he wanted to go to the food court and get something to eat because iirc he was pretty good looking. I was just very confused at what had happened at the time though.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 19, 2015 1:16 PM GMT
    Many many years ago I was sitting on St Pete beach near "Bedrocks", a bar I later found out was a gay bar. I had parked in their lot because they were not open at that time of day. Some guy sweeping up told me "you can park anywhere" with a growl. Odd, I thought.
    While on the beach, just relaxing in the sun, from one clump of sea oats over from me got up the sexiest, tannest most handsome built stud I've ever seen IRL. I was very green back then (I didn't come out until 35) and was probably staring (ok, I was!) and when he walked past me he said "Do you have the time?"
    Like a dumbass, I looked at my watch and told him the time instead of saying "Yes, do you have the place?" icon_sad.gif



    Some years later, as I was leaving a bar in Columbus OH--which until then was devoid of anything but twinks and queens--when coming in as I was leaving was a Colt-model worthy guy in jeans, suspenders and no shirt. Just as he glanced my way while I eyeballed him, I reached out and lightly snapped his suspender!icon_eek.gif


    He stopped, someone gasped (probably me) and smiled. icon_smile.gif




    We left together.
    icon_lol.gif
  • Hotgymguy22

    Posts: 98

    Feb 19, 2015 1:51 PM GMT
    I usually fail at trying to converse with guys I'm really attracted to. I remember in 2010 I went to Pensacola Beach on Memorial Day (I didn't go that weekend, just that Monday) and I was with a friend who was very outgoing. He stopped to talk to some guys and I was kind of standing there by myself. A guy with an Australian accent came up and asked why I wasn't talking to anyone. So I told him that I'm shy/reserved around a lot of people I don't know. He then told me he was from Atlanta and said that all of the guys around were his friends, also from Atlanta. He asked if I wanted to talk to any of them because he would introduce us. After some going back and forth him I relented and pointed to a guy that I found super attractive. He said that he was good friends with him and drug me over to meet him. I still remember him... Early to mid thirties, built, brown hair, about 5'7" or 5'8", his swim trunks were red and pink striped... Anyway... I meet him and I'm so flustered I can barely speak and what I do speak makes no sense. Shortly after I was introduced to him one of his friends came to ask him something and I left because I was so embarrassed at myself.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 19, 2015 2:01 PM GMT
    "Excuse me, but do you believe in The Hereafter?"

    "Why, yes, in fact I do."

    "Good! Then you'll know what I'm here after." icon_razz.gif
  • Posted by a hidden member.
    Log in to view his profile

    Feb 19, 2015 2:54 PM GMT
    Well, I was a horny little fucker so there was that cop when I was about 17--I had to get through his bullet proof vest--double shifting guard duty on a construction site where I was working after hours back in high school and then that bus trip to college at 18 when the guy I was footsying with wound up playing with me in the very back of the bus--see, segregation can be a good thing--for the remainder of our ride up to school; so there were a number of scores, but just an attempt? No, can't think of one that far back. Whatever Lola wanted...



    The tides turned on Lola though since hitting the late 50s. So the trick now is to be gutsy enough without being too creepy. It's a fine line, I realize, and the other guy probably doesn't judge it as I do. Oh well, that's life.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 19, 2015 11:46 PM GMT
    Few years ago when i was at a hotel for a week long conference, i'd always order room service for dinner after my workout... And the delivery guy was cute and made nice conversation each time he came to my room.

    I though it'd be fun to greet him each night wearing a little less clothes than the night before... Never seemed to scare off.

    Last night of my stay, he brought dinner up and i was just in a towel out of the shower... More friendly chat, then he asked if he could come hang out when his shift was over... Midnight he came up with a 6 pack, and i was still in the towel....

    He stayed the night. icon_twisted.gif
  • Svnw688

    Posts: 3350

    Feb 20, 2015 1:04 AM GMT
    @JonSpringOn

    tumblr_n1lwnsA4wY1smcbm7o1_500.gif
  • bobbobbob

    Posts: 2812

    Feb 20, 2015 2:06 AM GMT
    Mine was on my 46th birthday. It started out as a conspiracy between gay friends and my sons and their wives to get me back into circulation after my first partner died. There were at least 20 people at my house when I came in from an early happy hour. After that we did the gay bars and ended up at a downtown after hours bottle club with gays, straights, blacks, whites, civilians, tourists, navy and marines and every other type imaginable.

    I have no idea why or how a red headed sailor ended up at out table. He may have been lured by some of the women in the group. one of my sons, and I were sitting talking to him when he said the place would be all right if there weren't so many fags there.

    Big mistake. My son was ready to fight. The sailor was real fast to apologize and I jumped in to calm everything down. He persisted for quite some time in apologizing to me about it. in fact he was too apologetic.

    As things ended up he and I were the only ones at the table and just to have something to say at three in the morning, I said I was ready to go home. He stood up and pulled out his keys. I was stunned and tried to turn him down. Then he said he wanted to take me home but it was the way he said it, in almost an embarrassed whisper.

    I looked at him hard. He seemed harmless. I told my son what was going on and the sailor and I left the club. As we got to his truck I wanted to be sure he didn't mind taking me home and asked, "are you sure you want to do this?"

    He misinterpreted the meaning of my question and answered, "I've been thinking about doing it since I was fifteen, so yeah, I'm sure."

    I was wordless, completely wordless.

    He was a complete virgin to all things about gay sex so I went heavy on the rimming and other foreplay before showing him what an orgasm while being penetrated was like. I'll never forget the look on the boy's face. It was like all the mysteries of the universe had been revealed to him.

    We were regular FWBs for several months after that. My house is right across the bayou from the navy station so he was often there 2-3 times a week.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 20, 2015 2:11 AM GMT
    I've had patients flirt with me. Nothing overtly come on exactly. But flirt for sure. But it's unethical to date a patient.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 20, 2015 3:03 AM GMT
    When very young and naive a handicapped gay man convinced me to push him in his "malfunctioning" motorized wheelchair back to his apt. I started to get suspicious when acquaintances of his on the street all seemed very gay to me. Sure enough as soon as we got into his apt he started to come onto me. I bolted.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 20, 2015 3:49 AM GMT
    To make a long story short.My mom was very ill in the hospital and I was a wreck.I am the type who never goes to a bar before 10 pm lol.On this day..it may have been a Thursday.I stopped by the local gay bar around 8pm.It was just me and 2 drag queens.Out of nowhere walks this incredibly hot,muscular,long haired Latino in wife beater.I almost fell off my bar stool.I had already had a few.I went up to him and said damn you are so gorgeous.He was a lil embarrassed and we started to make out.We went hope that night and after a few months of separation we got together for good.Today is our fifth year together.icon_smile.gif
  • Posted by a hidden member.
    Log in to view his profile

    Feb 20, 2015 7:46 PM GMT
    I worked out one night with this str8,frat boy jock . After we finished he said I needed to go home and take a shower. Couldn't argue with that. So I go into the bathroom and start to take a shower at and in hops frat boy. He got what he wanted that night but turns out he was not str8.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 20, 2015 7:59 PM GMT
    Wyndahoi saidI've had patients flirt with me. Nothing overtly come on exactly. But flirt for sure. But it's unethical to date a patient.

    Perhaps, but it happens.

    Pre current partner, I once had a new doc in my physician's office (everyone there was gay) start stroking my legs and complimenting me on the musculature (I wasn't there for anything related to a leg.) Resulted in a hot affair. And a number of ski trips.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 20, 2015 11:16 PM GMT
    I was at a cafe in NYC over Christmas and one of the baristas and I kept looking at eachother and smiling. I was with a group of people and didn't want to be rude to them so as we were leaving I went up to the counter and asked him for a pen. I wrote down my number and handed it to him as I was leaving. He did text just 10 mins later but we weren't able to work anything out as I was only in town for the day...sigh oh well. I was pretty proud of myself tho as I never used to have the guts to do that. The mutual smiling definitely helped of course.
  • bro4bro

    Posts: 1036

    Feb 21, 2015 2:09 AM GMT
    There was a guy I'd seen in the gym for quite a while and always wondered about. We didn't usually work out at the same time so I'd only see him once in a few months, and although he sometimes looked my way he never gave me a smile. I was a little shy about approaching him; it's a very predominantly str8 gym.

    Well, one night I saw him at the gym and walked up and started talking. He turned out to be very friendly, and pretty quickly began fishing around for clues about my sexuality.

    I said, "Didn't you say something about going out for coffee?"

    He laughed, and wrote down my number.

    And then never called.

    Two months later I saw him in the gym again. I was OK with him being uninterested - but he came over, very friendly, apologized and told me he'd lost my number and asked for it again.

    And then never called - again.

    Fucking flake.
  • popobtc

    Posts: 74

    Feb 21, 2015 2:22 AM GMT
    Keep at it bro, I dated a guy that slipped a note into my pocket.
  • TheBaise

    Posts: 363

    Feb 21, 2015 2:38 AM GMT
    bro4bro saidThere was a guy I'd seen in the gym for quite a while and always wondered about. We didn't usually work out at the same time so I'd only see him once in a few months, and although he sometimes looked my way he never gave me a smile. I was a little shy about approaching him; it's a very predominantly str8 gym.

    Well, one night I saw him at the gym and walked up and started talking. He turned out to be very friendly, and pretty quickly began fishing around for clues about my sexuality.

    I said, "Didn't you say something about going out for coffee?"

    He laughed, and wrote down my number.

    And then never called.

    Two months later I saw him in the gym again. I was OK with him being uninterested - but he came over, very friendly, apologized and told me he'd lost my number and asked for it again.

    And then never called - again.

    Fucking flake.




    you're fucking hot. the dude must have been intimidated by you / he thought once the clothes came off, he wouldn't measure up. Nobody with any confidence would pass you by. Nobody any good, that is.
  • TheBaise

    Posts: 363

    Feb 21, 2015 2:43 AM GMT
    Met a hot daddy at a dance club in NYC and went home with him. As we got to his place, I thought / holy fuck, I've been here before! Went inside and I knew for a fact I'd been there before / about a year or two earlier. Looked harder at the guy, but I swear I didn't recognize / or remember him. I kinda wondered if he'd remembered me? He gave no indication. Jeez, so there we were going at it in his bedroom / kinda like re-reading a book you'd once enjoyed. Funny how slutty we sometime are / doing so many hook ups that we forget a guy's face / but remember his apartment.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 21, 2015 2:55 AM GMT
    popobtc saidKeep at it bro, I dated a guy that slipped a note into my pocket.

    I remember years ago eating lunch with a hot friend at a gay restaurant (attached to a gay bar). Waiter was cute. Upon giving him back the check with some cash, he said with a smile, "You didn't give me your phone number."
  • Posted by a hidden member.
    Log in to view his profile

    Feb 21, 2015 6:30 AM GMT
    I guess I haven't really made any, outside of the usual safe environments of the gay bar, bath house, or hook-up sites.

    When they've been made on me, I tend to be so oblivious, that I don't even realize it until it's too late. An hour, a week, sometimes even a month later. icon_rolleyes.gificon_eek.gificon_redface.gif

    Once I was in a bar with friends (I must be less intimidating when I'm with other people?) Three young people (two guys and a girl) came over and politely asked if they could grope my pecs. ...OK (WTF?) so they each politely had a feel while I did a little pec dance. We hung out for a bit, then all piled into cabs to go check out the lesbian bar... got lost on the way icon_redface.gif

    I once gave a talk in that big lecture hall in Davos where they have the world economic forum. (Not that...) Afterwards, in the crush, this cute blonde reporter asked if I could come up to her room for an interview. I was supposed to meeting friends for a beer, so I asked her to call me the next day... icon_rolleyes.gif

    Took this cute young guy on a scuba weekend. (He turned down a beer at dinner - turned out he wasn't even 21 icon_eek.gif ) I got the first shower, back at the motel, and laid on my bed, reading. He came out from his, naked, laid back on his bed, groping himself and said something like... I have a girlfriend and all, but... He didn't continue, so I didn't think anything of it at the time...
    icon_rolleyes.gif Good thing too... when I dropped him off after, it turns out he was my bosses, bosses, bosses son. icon_eek.gif

    Oh, it's horrible. The list goes on and on.

    So just what does it take to penetrate my skull? I remember a couple of different guys who actually turned around, dropped to their knees and bared their asses to me. Even I got that signal.
    Dang... I wonder if I still have their numbers?
  • Suetonius

    Posts: 1842

    Feb 21, 2015 6:52 AM GMT
    TheBaise saidMet a hot daddy at a dance club in NYC and went home with him. As we got to his place, I thought / holy fuck, I've been here before! Went inside and I knew for a fact I'd been there before / about a year or two earlier. Looked harder at the guy, but I swear I didn't recognize / or remember him. I kinda wondered if he'd remembered me? He gave no indication. Jeez, so there we were going at it in his bedroom / kinda like re-reading a book you'd once enjoyed. Funny how slutty we sometime are / doing so many hook ups that we forget a guy's face / but remember his apartment.

    I had a similar experience once. In the eighties, went home with a nice guy I met on Thanksgiving evening in a Castro Street bar. An artist who lived in a live/work loft. Had a great time - terribly sweet man, good-looking and sexy. Was also out and cruising Castro bars on Christmas night a month later. Ran into the same guy - he didn't recognize me. Went back to his place again, and again we had a wonderful time. After we were at his place, I had to convince him that I had been there with him before (Unlike Baise, I did recognize this guy before I went home with him, but kept it to myself). If I ran into him a few months later, we would have done it again, and I am convinced he wouldn't have recognized me then either. Didn't get his full name. Never saw him again. Considering when we met, I imagine he was one of those lost to AIDS.
  • being_human

    Posts: 152

    Feb 21, 2015 7:27 AM GMT
    *coughs*sluts! icon_biggrin.gif intriguing stories. Sadly I freak out at any advancement from a guy.. Hot or not.
  • Posted by a hidden member.
    Log in to view his profile

    Feb 21, 2015 8:25 AM GMT
    *I was kinda slightly tipsy and drunk in Rage, West Hollywood, a couple years ago. It was around 12 30 am, I was cruising the dance floor and saw this cute short 5'9 clean cut guy in an open white shirt. I looked at him, he saw me and smiled. Then he walked over and sorta exposed his chest/abs. I didn't say anything but smiled. He just grabbed my hands and put it right on his chest and he whispered in my ear **Like what you see?? I nodded, then he just pulled me in and just grabbed my waist and said **Want to come back to my hotel??. Lol, long story short, I hung out with him, found out he was some fiance manager guy from Chicago visiting. I ended up hooking up with him at the Marriott hotel by LAX. We had a wonderful hung out date the next day in Malibu. He texted and I texted back a bit after he flew back to Chicago but yeah, we just never kept in touch after that. Kinda shame! I think he was the only one that ever did that and I let him because he was cute and sorta my type. Anyway, I thought that was gutsy!or it could be I lose my inhibition and become an easy laid when I'm drunk?? LOL