A Bear's Tale #TBT: My First Time Sure Wasn't Like in Those Porn Movies
July 19, 2018
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My last #TBT, I left you in suspense.

I had a date with a man named Douglas and he had my clothes half off just before his roommate surprised us.

It was so embarrassing to get caught with my shirt literally over my head. But Douglas took it in stride and he called the next day with more apologies and offered to take me out on a second date.
Wow, this would be my first second date. That's huge in the gay world. Native young Kevin learned that oftentimes, the first date is it. Put out and get out or just get out for not putting out.

It had been a year since I came out and I was ready for my first time.

Since Douglas was sweet to follow-up and seemed genuinely interested in me, I decided that he was going to be my first time.

Of course, I did live with my mother so I needed to make arrangements at the Holiday Inn. I am sure a majority of hotel rooms are being used for people having sex. But in my mind, I needed to make sure the front desk staff thought I had legitimate non-sexual reasons for checking into a hotel in the city I lived in. So in the afternoon, I went to the Holiday Inn and while checking in I told them how much I appreciated them being in town because the paint fumes in my house were so overwhelming! Think they bought it but I bet they really didn't care.

So I had it all planned in my head. Douglas would pick me up, we’d go to dinner and I’d offer myself for dessert. My mother was going out with my brother that day so I wouldn’t have so many obstacles to overcome while leaving the house.

Before Douglas picked me up though, I needed to make sure all arrangements were made - a change of clothes, perhaps a bottle of champagne and perhaps a little whip cream. So I’d go home and gather all all of this stuff.

Mom is still there!! Why is she home? Where’s my brother?  “Running late.”


Well Ineed to get my gear over to the Holiday Inn. So I will put the whip cream, champagne and some chocolates in the bottom of a bag and put some fake trash on top of it. Then I’ll take out the garbage. That worked...no questions...good.

Now the luggage. How do I take the luggage? Maybe she won’t notice.

“Where are you going with that?” she asked as I tried to sneak by.

“Oh,” I said, “I am finally going to take it to have the handle fixed." Wow, that was a good one. “I didn’t know it was broken,” mom said. “Oh yes,” I replied, “since my last trip and that was quite awhile ago.” That worked too! Now the car was all loaded. I just need her to go away with my brother and let me be on my way.  To stay out all night I was already prepared to tell her I drank too much and was sleeping at a friend’s. This way she wouldn’t worry. But be gone already!

There was a knock at the door. Finally, my brother! But no, it was Douglas. He was early and my brother was late. Now I have to introduce him! My mother asked him to sit. And then my brother showed up. Great, we’re practically having a tea party. I tried to get them to go but they didn’t seem to be in any hurry. I mentioned how we needed to go so we can eat before a movie and we were off!

So Douglas and I went to the local restaurant Daily’s and had a very nice time. Things are going as planned at this point. Dinner was nice and I really didn’t want to go to the movie. After a year of the wrong men, nerves, anxiety and shyness, I am ready for sex. And Douglas was going to be the one.

Douglas was reading the dessert menu and asked me, as I rehearsed in my head, if I wanted dessert. So I said, and as corny as any movie I had ever seen, “Douglas, we can stay here for dessert if you’d like or I can be your dessert.” He smiled and said he’ll have me. And then I pulled out the hotel key and his smile grew even bigger and we were on our way.


To my surprise, I wasn’t as nervous as I thought I’d be. I was nervous all day but that all seemed behind me. I was about to do everything I only read about or saw in gay porn. I envisioned how great it would be to suck a man’s cock or to feel him inside me. Those thoughts were vivid and titillating. And now they would become true.

I enjoyed undressing Douglas and I so wanted to feel his cock in my mouth. As a get most of it in there, I didn’t dream about gag reflect. Damn, I kept rejecting it. I tried to work around it and didn’t want him to know I was gagging. Also, it tasted funky. I sure didn't dream about a funky tasting cock. Are they all this way? Douglas hasn’t even come yet and it tasted funny. To this day, all of these years later, I stills remember how funky it tasted.

Well, there are other things we can do - oral isn't the only option. So Douglas did start to fuck me.

It was very painful at the beginning and once again it seemed stranger - not as I fantasized about it. For one thing, I  farted a lot. I wondered if all men did while getting fucked. They certainly don’t show that in porn. I realized in this case, it was just air being released from my ass. Douglas likely didn't mind as he did cum and cum and cum. But I didn’t.

I don't know how rare this was at the time, but Douglas sure was a gentleman as he was determined to get me off too. Maybe I've gotten jaded over the years, but many a man who cum and then go. But Douglas would try to suck me off but nothing. He jerked me off in the shower. Again, nothing. He fucked me again while jerking me. Nothing. Oh my god, frigid! Later I decided I was just kind of pee shy or in this case cum shy. I ended up jerking myself off as Douglas played with my body and that worked. And then later the sucked me again and that worked - even with whipped cream!
The aftermath...

Well, I learned a very important lesson when it comes to food and sex. Don't use whipped cream - at least make it non dairy. While I showered several times, over the following few days, my groin smelled like sour milk. Yuck.

If that wasn't enough, I developed these weird bumps inside my mouth. They multiple and grew bigger. So I went to the doctor. The doctor was puzzled by what I had - Oral Thrush. She said babies usually get it by sucking on unsterile nipples. I told her that I engaged in gay oral sex for the first time and that’s probably how I got it. She said probably. The doctor said my partner likely had a yeast infection. I told her it was probably a good idea for my medical history that I confessed to her that I was gay. And she said, “Not really, but thanks for sharing.”

I told Douglas of this and he was quite embarrassed. He also never called me again. So is it a two day stand?

But besides finally having sex for the first time, I also came home and faced my mother and decided there's no time like the present then to come out to her.

For that story, you'll have to wait for another Throwback Thursday.

#TBT #ABearsTale #ComingOut #GayComingOut #FirstTimeGaySex #GayBears #MyFirstTime

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