The First Time

After the most confusing New Years ever, I went back to my hometown to visit for the first time since I came out.  No one said anything.  No one asked any questions.  I would have rather everyone call me a fag or sit me down for an “intervention” than no one say a thing.  I wanted to be accepted and be just as interesting as everyone else but my “new” lifestyle was too controversial to discuss (with me in the room at least).  When I came back to San Francisco I was determined to get laid.  I didn’t care about the romance anymore.  I was 27 and had wanted to have sex with men my whole life and was done waiting.  I knew I could find it, I just hadn’t wanted to go down that road…until now. 

I had turned my Manhunt account on and off since I moved to the city and decided, without better knowledge, that I could find my first there.  It didn’t take long before I started chatting with a man that lived downtown.  He was successful, lived alone, was down for no-strings-attached sex and was interested.  We chatted a few days and then decided to meet at his house one night.  He gave my name and photo to the front desk so they’d allow me in the building and then I headed up to his apartment.  He was shorter than I thought he was going to be but he was cute.  He was 40, swimmer build and was quite the gentleman.  He opened a bottle of wine and we sat on his couch and talked about our jobs.  We finished that bottle and he went to grab another from the kitchen.  When he came back he sat much closer than before.  I was thankful for the wine because I was nervous even having drank it – no telling what I would have felt like without it.  We finished one glass and he put his hand on my leg.  “Here we go,” I thought.

He said, “You’re really handsome,” and leaned in and kissed me.  We made out for just a couple of minutes before he asked if I wanted to move to his bed.  We got up and moved to his room.  As he took off his clothes, I sat on the bed – the completely white bed – and he said, “Oh, wait, not on the duvet!”  I leaped off and he politely folded it down to the end of the bed.  At this point I was assuredly drunk.  He was blowing me and stopped to ask if I did whippits.  I had no idea what I whippit was at that point (inhaling nitrous cartridges) and said exactly that and he didn’t respond.  He moved up to my neck and then to my arm pit and says, “Do you use deodorant?”  “Yes,” I respond.  “Oh, don’t do that.  Stop.”  I’m confused as to why you wouldn’t – eww right?  I hadn’t thought of ever not wearing it.  Yet again we moved on past the random interference of his demands and I kissed and nibbled on his neck – he stopped me, “No biting.” OK.  Then I run my hands down his back with my fingernails grazing his skin – he stopped me, “No scratching.”  Jesus, seriously?  He asked me if I wanted to fuck him so I grabbed a condom and his lube and fucked him for a few minutes – I don’t remember that part very clearly – then he went to fuck me, I remember it hurting a lot and telling him to stop.  He asked, “Are you clean?” which I knew I was.  I asked him the same and he assured me he was so he took off the condom and fucked me bareback – it felt better the second time but wasn’t my favorite for sure.  He pumped for about a minute and jumped up to my head and came all about my face before I knew what hit me.  


I was in shock – not bad-shock, but stunned.  I couldn’t even think of cumming.  It was all a lot to take in.  He went and got in the shower and I followed him in shortly.  I got in with him and he rinsed off really quickly and hopped out super fast.  I went back to his room and he asked me to spend the night so I laid down and slept in a bed with a man, naked, for the first time in my life.  We woke up in the morning, walked to the corner Starbucks and I bought us coffee, walked down to the Embarcadero and parted ways.  Said we’d see each other again but we never did.  He had a lot of rules and truly wasn’t that attractive to me.  Although, technically I had just had my first gay sex, I was so drunk that it was a blur which made me sad.  My first time ever having sex was very memorable, not planned, but exactly what I wanted it to be.  This was not, so I was thankful one of my firsts was a beautiful experience.

You should know better. You, you. You. You. You should know better than to fuck with me.

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Sometimes I take a shortcut right before I get to a destination...

I gave dating a break after that.  I still cruised on Manhunt and played the match game on OkCupid but no one was going to get my attention when I had two bottles of two-buck-Chuck to kill every night.  I started to make it a game with myself to see how much I could drink before I went to bed.  My next jaunt into dating was a man from OkCupid named “Dave” and Dave was a very tall Asian man who appeared to be more masculine in photos than he was in real life.  I arrived in the Castro via the train and had been bundled up with a scarf and jacket because it was cold on my side of the city.  The sun was out in town and he had a short sleeve shirt and flip-flops on.  First interaction in person:

                              Dave: You’re all bundled up!

                              Me: It’s cold and foggy in Daly City!

                              Dave: That’s because of all of the rice cookers.

I didn’t expect him to make a racist joke so soon but he went for it right out of the gate!  We had brunch in a café in the Castro and he was nice.  Not my type, we had little to nothing in common and he had a terrible flakey lip situation.  It was not cute.  The following day I had settled into the cold that was hitting me the day before and I got a Gmail-chat message from Dave with lots of emoticon smileys and things.  I told him I was sick with a cold and he responded “Cuddles! J”.  It sent shivers through my already sickly-feeling body.  Cuddles??  Who says that?  I didn’t know how to respond with a rejection without actually saying it out loud so I said, “My cat cuddles.”  He just said, “Ouch.”  We never spoke again.

Since the OkCupid route wasn’t going my way and I was damn tired of being a gay-virgin (because the tragedy that was sex with Teach was not and still is not being counted as intercourse…in my opinion) I put all my eggs in the Manhunt basket.  I found a gorgeous headless torso that liked my headshot enough to unlock his naked picture that had his face…sort of.  His body was amazing.  We exchanged numbers and decided to meet one day.  While shopping in the grocery store one day I saw a checker that I had met on the college campus with my friend the year before.  He was adorable and had a boyfriend when I met him.  I went through his line to check out and tried to talk to him like he was my friend and he responded.  He was a huge flirt anyway but I bought it.  I went home and stalked his facebook, sent him a friend request and after he accepted made no move at all.  I didn’t know what to do next.  I had never asked someone out before.  The Teach and the dude from my second ever man-date had made the first move.  Shortly after he sent me a message asking why I hadn’t asked him out yet.  Stupid me.  So I did.  

The morning of my date with the checker, hereby known as “the Pixy”, I woke up very horny.  I had no intention of trying to have sex with the Pixy on our first date but the sexy stranger from Manhunt would do.  I sent him a text asking if he wanted to come over.  He responds saying he has a business lunch but he has about thirty minutes so I gave him my address.  I had never done anything like this in my whole life.  He called and said he was downstairs so I run to let him in and he is tall, dark and super hot.  He is in a button, tie and slacks that are tailored to perfection on his ridiculous body.  We walk inside and he says, “Where’s the bedroom?”  I show him into my room and he grabs me and kisses me.  I’m stunned because he is that hot.  He starts taking off his clothes so I do the same and he throws me down on the bed and goes down on me.  He takes a break and crawls up and kisses me and then faster than lightening strikes he was sitting on my face.  It was so fast I cannot describe.  Here’s a first.  Kinda shocking, kinda hot, kinda confusing.  He then went back to his original position and did the same to me…but for like ten minutes.  Ridiculousness.  I had no idea anyone would ever do that and I was happy to have met him.  He looked like he was certainly ready to fuck and God knows I wanted to but his dick was enormous and I didn’t want my first time to be my last time so I kept stalling until he had to go.  I totally blue-balled him.  It was all too intense and I didn’t even know him!  He went to wash up and when he walked back into my room he crossed my cat and he asked its name.  I told him and then realized I didn’t have a clue what his name was.  We just did all that and didn’t even know the others name.  Holy shit, who am I?? 

The rest of the day I spent anticipating the date with the Pixychapstick, which he applied religiously all night long, and I noted that it smelled just like Fruity Pebbles.  Basically I wanted to kiss that smell right off his face so I looked at him, paused for reassurance that he wasn’t leaning away, and went in for the kiss.  Accepted.  He coyly pushed me away telling me he never kisses on the first date.  So I kissed him again.  The bus shows us and we run to get on.  I sit next to him and thirty seconds after we’re moving he says, “You can put your arm around me now.”  Laughing, I do exactly that.  He fit there very well.  When we got to the end of the line we started the fifteen block walk in the drizzle towards his house which was first on the way.  We walked holding hands and pulling each other back and forth.  During one long stretch of chain-link fencing we repeatedly, drunkenly, and frankly adorably fell against the fence allowing it to hold us up while we made out more.  I dropped him off at his apartment and walked home in a daze of happiness.  This is what I needed and on the road to what I was looking for.

If at first you don't succeed, stop drinking and try again sober...

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