Drive bys and Self Esteem

I only work a half day today, many errands to run as we prepare for our big event. I'm transporting my mother in law today, so will have some windshield time to sit, think, and listen to my favorite podcasts.  Driving has always been something I enjoy, I suppose it's the fact that motion sickness takes over if I am stuck in the back seat and can't see the road.  I blame my father, who couldn't even go out on a boat without feeling nauseated.  Plus, I like being in control (foreshadowing, perhaps?  doubtful.)

When I drive any distance I like to see if I can find a quick stop somewhere and scrounge up a little fun.  This path takes me past a couple of major metro areas, so opportunity is sometimes there.  It's a crapshoot, and many times I get my hopes up and then it doesn't work out.  Why am I disappointed when that's the outcome?

I've struggled with low self esteem my entire life.  I was a sensitive kid, bullied a bit through school (nothing physical, just name calling and social shunning), didn't have any girls interested in me until halfway through my senior year, and never fucked one until i was 19.  Never really though I measured up, was not willing to risk going up to a girl and being rejected.  I'm told that I have nice equipment - by guys, I've never had a girl tell me I had a big dick, or was a good lay.  I suppose if I would have had some positive feedback from the female side of things, it would have helped me feel better about  things. 

It's funny.  By and large, I'm a very confident person at work, at home, out in public (I referee basketball and know I do a good job, don't take any crap there).  But I'm filled with insecurities when it comes to acceptance and rejection of me as a potential partner.  Does it all go back to my lack of success as a young person?  Why do I care what other people think of me, especially randoms on a Grindr or A4A? I need to get over myself in that area.

On my travels, I've run into guys who are really into my whole "Daddy" vibe, I suppose in the bigger cities there's much more opportunity for people with specific wants and needs to find each other.  I still occasionally communicate with one of my former hookups from Chicago, wishing we could find a way to get back together.  Hot HOT younger guy, who was really into me.  I could get used to that attention.  And you would think that would help with my insecurities. It probably does, if I allow it.

OK, so I've begun to tell my story, with a hopefully related sex story at the end.  So, here goes.

I was in Chicago for a conference.  I came to this particular one each year, with mixed success in the hookup area.  Too many missed connections.  This time, I placed a craigslist ad, and hoped for the best.  I actually was searching for a MW couple, thinking that would be totally awesome and fun.  I think that's true for me, but I still haven't made it happen.  C answered the ad, said he had a girlfriend that might be interested and he was bi-friendly.  We communicated, did a little dirty talk and fantasized, and arranged to connect when I got to town. 

Needless to say, I was worked up by the time I arrived.  Dropped him a quick note, he was working, but arranged to meet me after work at a restaurant/bar a few blocks from my hotel.  I texted him, and he said he'd meet me out front.  I waited, but didn't see him.  I suppose we should have given descriptions to each other besides "6-2, 210, brown hair". 

I text again, and he said he was with a group, but had told them he was meeting a friend.  He'd be right out to get me.  Now, in all the talk, he'd really never described himself all that much.  So when a tall good looking black man waved me over, I was stunned.  If I looked like that, I'd tell and show everyone!  We quick hugged, and headed in to the bar.

He was with a group of 5 or 6 others, and we had a nice time, a couple drinks, and many hidden text messages back and forth.  I still was having a hard time believing this stud would be interested in me. (See above...)

I did have meetings in the morning, so a little after 10, I begged out of the gathering, and C offered to give me a ride back to the hotel.  Being a good visitor, I invited him up to the room for the marvelous view of the river and downtown.  Once in the room, this magnificent beast took me in his arms and kissed me hard and deep.  We spent a nice amount of time pressed against each other on the bed, kissing and touching each other. 

I don't remember whose or what articles of clothing came off first, but once it began, it wasn't long until we were completely naked, and I was blowing him as best I knew how.  A 69 followed, with hands, lips and tongues all over each other.  By this time, I wanted him in me so bad, and he was more than up for the challenge.

After eating my ass like it was his last meal, he slid into me, and we were finally connected.  Sometimes I would be hard pressed to remember any details about a hookup.  This one, however, I have such vivid memories of.  The softness of his skin, the taste of his lips.  The feel of his ass flexing as i pulled him deeper into me.  The fullness I felt, and the emptiness when he pulled out and sprayed my chest with his cum. All of these sensations are still with me after years.

I cannot wait to figure out how to hook up with him again.