The Last Frontier - I Hope Ch. 02

So if you have read my work you know that I mostly write about my experiences getting massages, mostly Happy Ending massages. These are all true stories, and I hope my writing reflects that. While a lot of these happen while I travel for business, they also happen at home in Texas. Sometimes they are basic hand job happy endings and sometimes they are full on sex. When you start down this road, you do not know where it is going to end. I may have reached my limit, let me know what you think.

Two months later I decide again that I would like to experiment with a gay massage, again. I was surprised that I enjoyed it so much on a sexual level, and that I had no problem maintaining an erection with a guy. I am beginning to think that sexual feelings are all in the sensation, and hard and fast sexual orientation divisions are man-made.

So while I wanted to try this again, I was looking to find an actual spa that is gay friendly. I would be happy with a Trans spa also. But, while there are millions of heterosexual rub and tug massage parlors, there are few if any that will give gay or trans erotic massages. For these massages, you typically have to go to someone's house. While I did this twice for two beautiful TS women, I would have rather go to a spa than a home for an experimental gay massage.

My work travels recently took me to Philadelphia, and I found a spa online that offered men for men massages.

I booked a session on line, and visited at the end of my business meetings.

It turned out that this was not an actual "spa", but just a rented room in a commercial brownstone. At least it was not in anyone's home.

I showed up and met Jim. An older guy maybe 62 or so. He welcomes me in and I see that there is one small room and a small bathroom. He shows me where to hang my clothes and we chat while I strip down - there was no place for him to go to give me privacy and I think that would be kind of strange, since this is expected to end with at least a hand job.

So I get naked and I sit on the massage table to discuss problem areas, and how deep I wanted the massage, I eventually lay down on my stomach and we start.

It was a very good massage, he had a lot of experience and was very strong. Ten minutes into the massage Jim made the same move Tan used. He started letting his cock rub up against my hand. I grabbed it pretty quickly and started rubbing it. He quickly dropped his pants and flopped his dick into my hand. IT WAS BIG.

He was still relatively soft, but his dick was long and heavy. After a minute or two he came up to the side of my face, and placed his dick right up to my lips and said "Open up". I opened my mouth and he slid his dick in.

He kept at it for about two minutes and over that time he went from soft to very long, hard, and curved like a banana. When facing him it curves upwards, so with my face on its side, it was threatening to poke me through the cheek.

To his credit, he pulled out and continued the massage. I was wondering if the massage would end early since the sex had started. I like the happy endings, but I like to have a real massage first.

Jim kept up massaging my upper back and his hard dick would occasionally slap against my side. In about five minutes Jim came up to the very end of the table and started massaging my neck and shoulders. He just laid his dick on the top of my head. He ran his hands below my neck and asked me to lift my head a bit so he could finish my neck.

I should have seen this coming, all he wanted was the opportunity to shove his dick way into my mouth. He was way too big and thick for me to take him all the way in. I tried to do this as much as I could. I grabbed the base of his dick and stroked it while I sucked on the first four inches.

This wasn't good enough for him, he removed my hand, lifted my head, and started saying "Feed on it. Feed on it."

I don't know exactly what that meant, but it didn't matter. He took control and started roughly fucking my face. He only stopped occasionally when he tried to see how deep he could go. I finally found out what deep throating means. He found my gag reflex point many times, I thought I would throw up on the floor.

After a few more minutes of this he went back to the massage. Now he was doing my lower back and ass. He would reach under and stroke me enough to get me hard. I had no idea how far this would go. I didn't know if he would fuck me, or if I would fuck him, or just end as a hand job.

The massage continued for 15 minutes with each of us occasionally stroking each other. This was very enjoyable, and there wasn't much talking. I found out that was an important point.

Jim reached under for the last time and stroked me so much I wound up lifting myself up on my knees to give him better access. Once I was hard, he had me roll over onto my back.

He started giving me a hand job, and even took me into his mouth a few times. Then the tone of the visit started going badly. He started speaking to me. He spoke to me about what he wanted to do to me, and always referred to himself in third person. He started explaining to me that he had a couple of young studs that he brought in if a four hand massage was needed. Honestly I considered a four hand massage, they are way more erotic.

He started searching his phone for a photo of his guy. All the time explaining to me what he and the guy would do to me. Well I figured the guy would fuck my ass, and I would be ok with that. Maybe I would blow him also. What I was having a problem was this guy talking to me so much.

During this I started stroking myself to stay hard, and he playfully chastised at me that that was his job. But I was having trouble maintaining my hard on, with him talking to me. I kept stroking myself and finally saying "I don't care about his photo." He still wanted to show it to me and he still chastised me for stroking myself, and I lied with exasperation "You don't understand, this is my first time with a man!"

I thought this would make him pause, but it didn't. He showed me a photo of a young stud cumming all over the belly of another massage customer. The photo didn't do anything for me. I kept on trying to maintain my hard on.

He finally took over the hand job and said "First time eh?"

And I said, "Well not technically, I have been with a few Transsexuals. But with them, there is no massage, just sex. I was hoping to try a massage with a guy that would also have sex. I wanted to try oral a bit more, and you certainly checked that box."

He said he was glad he satisfied that curiosity. And boy did he! That was a huge cock with an unfortunate (for me) curve. The curve would probably be great for penetration into anything but my mouth.

He picked up the pace, used his mouth one or two more times and then I finally blew my load.

He got a hot towel and wiped me down and said "Typically this is where everyone gets self-conscious and hurries up to get dressed and split. But give me a few more minutes for the massage."

I wasn't self-conscience about laying there naked after an orgasm, so I gave him ten minutes to finish the massage.

Overall, the massage was pretty good, not expert. However I think I learned an important lesson. I still agree with my initial premise that sexual divisions are not black and white, and that sensations feel good no matter their origination. However, I think I am too straight to do a sexual massage with a guy with my eyes open with him speaking to me. It just took me out of the moment and I struggled to stay engaged. With Tan it was easy. He did not speak, he had a very slender body, an ass that would be great on a chick, (honestly he had the smallest dick I ever could imagine but that is a different story), and he kept my eyes covered.

Jim had a huge dick. That didn't concern me, I was into it. I got a lot of oral practice. But the more he spoke to me the harder it was to stay enthused.

This may be where I need some advice from the readers. What do you think I should do next? I love heterosexual massages, obviously. I liked 2 of 3 of my transsexual massages, even if I was disturbed a bit. I liked my first gay massage, but the more masculine one had good points (oral) and bad points (him speaking). Where do you think I am on the sexual spectrum?