missed 1st times

woman_inside

Really Really Experienced
Joined
Jun 9, 2006
Posts
331
any opportunities you'd wished had been your first lgbt time?

I was once fondled on public transportation, it got me so, so aroused that if he' suggested going to a hotel i'd lost my anal virginity to him. sometimes i fantasise that he offered me money, we went to a sleazy hotel, he had me dress like a slut and i got on all fours for him to fuck me.

another was a lgbt society halloween party, maybe if i'd gone and gone in drag, looking 4 a stud to take me home.
 
A few years back I was broke and had no car. I was at a bus stop on a busy road at rush hour, going to my storage unit to get some things for my apartment. This guy stops and offers me a ride. I didn't recognize him but I worked in a busy little store nearby, so I figured he knew me from behind the counter. It was damn hot and the fumes were bad, so I gladly took the ride. I advise against it normally but I'm a big dude with some martial arts training and I had a knife, so I felt ok. It wasn't a mile before he good-naturedly started asking details about my cock. At the time I wasn't really curious; there were a few short thoughts but nothing like lately. I was very uncomfortable, but I'm a bit shy and even if he'd been a woman I'd have been blushing through my tan anyways. Besides, I had a girlfriend and I wouldn't have cheated. I got out before my "stop", and thanked him (I was very appreciative of the ride!). Now, I think about it, and he probably wanted to just suck me off.
Then there was the girl at that ice cream shop that just, out of nowhere, started talking about how gay and bi guys were her FAVORITE thing in the world. WISH I KNEW HER NOW!
 
For me I have several missed first times and well have yet to have a first time. I look back at 3 of them with some regret but they must have not happened for a reason and maybe someday it will happen but if not thats ok too. I know that sometimes fantasy is better than reality anyhow.

1. My ex girlfriend had recently introduced me to joys of anal sex, recieving that is. She really wanted to see me with another man. At first I was reluctant but I became a bit more receptive and she first wanted to set me up with an ex (bi) of hers but he was huge (she had an old picture) and was scared to death of something that big in my ass.

She upped the size of the toys we were using and we had a meeting with him I let him know I was scared and he suggested we wait till I was more comfortable (now I look back and should have at least blown him). She tried once more with another old friend of hers that she was going to give a sympathy fuck to and have me "walk in" as she knew it was a fantasy of his. I had to work late and got there about 10 min after he had finished and left. :(

2. After she and I broke up I became very bi-curious and went to adult store hoping to find a glory hole I didn't know if could go thru with blowing a stranger but figured a nice lubed handjob was something a guy might not turn down. I forgot to bring lube and bought some and some tokens and headed back to the arcade. I was back there almost an hour and gave up that anyone would show up.

I started back in the store to look at gay/bi vids. The clerk approached me (good looking blonde surfer type) and told me he might have what I was looking for and that he was off the clock in 1/2 an hour. He also mentioned he lived about 3 blocks away and we could go as far as I wanted (and that protection was a must, big plus for me). He seemed really cool but something seemed wrong about the whole thing (just seemed to good to be true). The store got really busy and I ducked out.

3. Most recent was my best friend of 10 years used to get drunk at each others places and crash. At first he started to make comments that seemed like he was making passes at me. My girlfriend (now wife) even caught one of his passes and mentioned it to me giving me the green light to experment if I wanted to, but I still wasn't sold. One night we were playing video games the girls out of the house and he just blurted out that he needed to confess something, that his girlfriend hadn't been his only lover. I was confused but then he told me that before they started dating he had sex with a couple of his guy friends and liked it. I was so stunned I couldn't say much and he changed the subject quickly. For about a month not much was said.

Then one weekend his gf was out of town and I came over and we were talking and he brought it up again in much greater detail. I could tell by the outline of his hard cock in his sweats that he was turned on and I wasn't hiding the tent in my pants either which he kept glancing at. Finally he ended his story and I told him that he should feel lucky for having such an experience and not guilty (he said he felt guilty for never telling his gf). I added that I wished I would have been able to experience it too. I paused hoping that he would take the next step but there was nothing and the tension was building so I then add "If you ever feel like experimenting again please let me know". He seemed outraged at the notion and made me swear never to bring it again. But at that moment (disapointing as it was, also since our friendship never recovered) if he had said yes I would not have hesitated to do anything he wanted. I often think of what a great night that could have been.

Sorry to go on and on but I often think of these times to ponder "what if?"
 
Parking cars downtown when I was 17. I did the after work rush. A regular customer who was always nice to me invited me over to his place when I got off work. He would come and pick me up and we could hang out and party at his place. He was probably mid 40's or so. I could not do it at the time, but I sure wanted to. This was not really a missed opportunity as a few months later in the summer he invited me to a party. I went and it was a lot of fun. This time he convinced me to stay when everyone had left. I did and it was every bit as good as I thought it would be months eariler. We spent most of the next day in bed also. He was gentle and nice and treated me well. He had a nice cock and he knew how to use it. He wanted me to stay with him, but I simply could not. We did see each other quite a bit for about 6 months. It was very nice time. When he fucked me I always felt so good. A very nice time and I was glad for the second chance.
 
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