I’ve always been…

Shy.  I know that there are people in my life who find that amusing.  Put me in a room with people I know, and a few beers, and I’m chatty-fucking-Kathy.  But, you put me in a situation where I’m among people I’m not familiar with… and I, most times, have turned into a wall flower.  I’m working on that.

Recent history – I’ve started getting to a point where I feel more comfortable putting myself out there.  What does that mean?  That I’m horny, and I want to get laid.  You cannot get laid if you do not put yourself out there. Well, almost… you can pay.  I've done that in the past.  Not often, but I don’t see a problem with it.  It’s paying for a fantasy.  What I’m starting to find – after a fairly impressive amount of weight loss – is that I want to meet people, have sex, and not pay for it.  Interestingly, one paid experience recently gave me more confidence to go out and meet guys.

My birthday is early in march, and as is fairly typical for me, I like to treat myself in some way to commemorate.  Often it’s a hair cut, or a new tattoo, or a massage.  I have been going to the same guy for a couple of years now for massage.  Great guy, therapeutic, very ‘on the up and up.’  No shenanigans.  However, he was unavailable.  Which opened the door. 

A guy that I’d been chatting with online indicated he’d be in my fair city (admittedly, I live in the ‘burbs and it was a 45 minute train ride INTO that fair city… but a nice get away).  So, knowing full well that this might be a bit more sensual than therapeutic, I booked an hour of his time.  Taking the train in I was a bit apprehensive, but excited none the less.  I don’t go into the city very often, but it’s nice sometimes to walk around.  I planned a full afternoon of it.  Massage, then treat myself to an early dinner, and maybe have a couple of beers at a local gay bar.

I got into the city early.  Had plenty of time to kill so I walked from the station.  It was a little gray and drizzly.  Not overly cool, though.  I walked around, took in some of the historical sights, made my way to his hotel.  I was still there early.  I killed time until it was ‘time.’ Knocking on his door, I was nervous.  While he opened the door, I was telling myself just to breathe, and relax.  Since the day was a bit warm, and I’d walked around, I was a little sweaty so he offered to let me take a shower.  Which i did.  He was very personable, and very muscular, and very pleasant to both be around and look at.  when I had come out of the shower, I noticed that his laptop was up – and porn was playing – in addition to the soothing music I usually associated with massage.  It was an interesting juxtaposition.  And, oddly, made me feel more at ease.  I don’t think I’d really thought about it until then, but I was concerned that I might assume something was going to happen that, in essence, wasn’t part of the program.  That let me know that I wasn’t off base in my expectations.

Then, I was face down on his massage table.  Naked.  Not even a towel to drape me.  While I laid there, he dropped his shorts – the only clothing he’d been wearing.  He started out by standing at the head of the massage table, close enough that I could feel his dick brush my hair.  He worked on my upper back, applying pressure… rhythmic compressions.  I could feel his dick, soft, against the top of my head.  I started gently rubbing my hair against him, hoping he’d get that I was enjoying it.   After a few minutes, he moved down my right side to work on my back.  He took a moment and walked to the dresser, I wasn’t sure exactly what he was doing until he came back and laid his hard dick in my right hand.  He’d lubed it for my convenience. :)

It’s at this point that we left all the pretence of therapeutic massage behind.  His dick was substantial in my hand.  It felt really good, really solid.  Still working on my back, he moved lower touching my ass.  I cannot tell you the last time I’d had attention paid to my butt.  What I can tell you is that he knew what he was doing.  I felt him pull my cheeks apart, and start to finger my butt hole.  And I gasped.  Not in pain just in surprise – I can’t say it felt ‘good’ cause it was so much less and more than that.  It was just this visceral feeling of ‘oh god.’ 

He played with my hole for a while, opening it up and, eventually, finger fucking me.  It felt so different from what I’d felt before.  I was a little scared because I thought I saw where this was going and his dick was not a ‘starter cock.’  He talked to me the whole time, both encouraging me, and talking dirty.  I don’t recall everything he said, he could have been speaking a different language.  “Pussy boy.” “Good boy.” all of it sounded the same.  I was so focused on what was going on in my ass. 

He was so hard.  He moved to the bed, and told me to eat his ass.  I still remember his clean, sweet ass and I buried my face in his crack.  Mouth, nose, chin… almost like I couldn’t get in there far enough.  I stroked hid hard dick while I did.  Played with this nipples, while I did.  I loved him telling me that I was doing a good job.  That I was a good boy.  “You like to take care of your daddy’s ass, don’t you?”  All I could asnwer was “hell yes.”

At a certain point, he told me to get onto my back.  That he was going to give me more than his fingers.  and I was nervous.  And I told him so.  “Trust me.” so. I trusted him.  I noticed as I rolled over that I had ropes of precum coming out of my own dick.  Ropes.  I don’t use that term loosely.  I was pretty amazed.  When I jerk off, 95% of the time I use lube.  Here I was with a puddle of precum, and we hadn’t even kissed. 

He lubed my ass, and his dick.  Pulled me to the end of the table, so he had a good angle.  Then he started just playing the tip of his cock up against my hole.  He started moving it in, and I had to stop him.  There was pain.  Once again, he told me to trust him.  He also put some different lube in me – I can’t say for certain is was desensitizing.  What I can say for certain is that he took his time and slowly moved against me.  Before I realized it, he was balls deep in me.  It didn’t hurt, just felt really – god, how to describe it – felt really right.  He started moving side to side – not in and out.  So intense.  Thinking back on it, I loved the feeling of his furry thighs against my ass. 

As he was playing in my ass, he had me stroke my dick.  It was so intense, but I didn’t cum.  I think because it was so intense.  I didn’t cum, and I didn’t care.  I laid there, feeling my breathing returning to normal.  Hey, just cause I didn’t cum didn’t mean there wasn’t heaving, and sighing.  I took a shower – second one in his bathroom.  Cleaned up, I felt good.  afterwards, he let me rub his back, scratch his back.  It was really relaxing.   I got to see that incredible butt again.  I could kiss that triangle right above his crack, kiss his back as I rubbed it. 

When our time was up, I went on about my day.  I felt validated, for lack of a better term.  I enjoyed what I did, and was encouraged by him, told I was a good boy.  I was approved of for what I was doing.  Spent a few days putting my head around that.  I liked that feeling.  You know, when you’re really overweight – or, more, when I was extremely overweight, the last thing that seemed appropriate was for me to be sexual. I know that’s my hang up, my baggage to deal with.  It was very freeing to feel able to be sexual and for it to be alright.