tagGay MaleAutobiography

Autobiography

byCourtStJester©

Many of you have written asking about me and my background (including sexual experiences) although I cannot understand why you would think them to be interesting. Maybe you would like to analyze my background to see why I write about the things I do. Maybe you are just curious. OK, this is my story.

I only had one homosexual experience before I became what I considered to be bisexual. From that experience until I was 38, I lived a straight (albeit mildly curious) life. What I will write about here is my first experience and later I will follow up with what happened 20 years later. Since this happened 40 years ago, forgive the addition of details that may or may not be accurate but don't detract from what actually happened.

I grew up in the Midwest about a two-hour drive from the closest big city. I was the smallest boy in my class and considered a nerd (we weren't "geeks" back then) and was very naïve. I was a good Catholic (and, no, my first experience did not involve anyone in the church) and an altar boy until I was 17.

Sexually I was about as uninformed as you could get. Dad had died when I was 9 and mom had avoided the "birds and bees" talk. The sexual revolution may have started in the '60's, but it hadn't reached our town (don't think it has even today). My friends and I were more interested in sports than girls and never did more than hide behind the shed with a copy of Playboy.

About that same time my best friend's cousin came to live with him. His real name was Roger but we called him SB for "surfer boy". Roger had lived in San Diego and his parents had sent him to live with his aunt in the Midwest, although we never knew why. Someone said that he got a girl pregnant or was caught trying to. What ever reason Roger, at the age of 23, was sent packing and landed five houses away.

Roger was an instant hit. He was from the big city and had a big city feel. He was cooler than anyone else in the neighborhood. He dressed great, was as handsome as a movie star and in great physical shape. All the guys liked him because he was a good athlete. The girls loved him, although when I think back I cannot remember him ever dating any of them. Rather, he would go out with a pack of them like he was one of them. Most of us did not have "gay-dar" in our town so this, too, went over my head.

When my 18th birthday approached, Roger offered to take me to the "big city" to buy clothes as my present. He asked my mother (yes, I needed mom's permission even at 18) if it would be all right to take me in on Saturday and come home Sunday. I guess mom's "gay-dar" was working and she suggested a day trip. So on Saturday, an oppressively hot day in August and which was actually the day after my birthday, we boarded a train at 7:00 a.m. and headed for the "big city".

We arrived at our destination around 10:00 and started our shopping spree. Shirts, pants, suit jacket, underwear and not the stuff that moms buy. This stuff was cool. It was hip. It was way out of my league.

At about 1:00, Roger decided that it was time for lunch. This was also his treat and he took me to a nice restaurant. Since the drinking age was 21, I ordered a Coke and a burger and he ordered a steak and a rum and Coke ("Make it strong" he added). When the drinks came, he poured the two together making two decent rum and Cokes.

"This is a special day," he said clinking his glass against mine. "Today you are a man."

I was pretty proud of myself. Roger had taken me under his wing and wanted me to look good. He was even letting me drink, although I asked him not to tell my mother.

We continued eating and all the while he explained what silverware to use and where to place the napkin. Boy, did he know a lot of stuff. I was impressed with him, almost to the point of having a crush on him.

Roger ordered another couple of drinks and remixed them again. By the end of lunch I had a little buzz on. We were planning to do more shopping, but Roger suggested something else.

"I have a friend who works at a hotel down the street," he said. "He can let us use a room where we can try this stuff on. That way if we don't like it or it doesn't fit, we don't have to come all the way back to the city to exchange them."

That made plenty of sense to me. Roger paid the check (WOW, he spent $40 for lunch for me.) and we headed down the street with our packages. On the way, we made a stop at a liquor store where Roger bought a bottle of rum and some Coke "for later".

When we got to the hotel, Roger suggested that I wait in the lobby and he would "see if his friend was working." That was fine with me since the hotel was air-conditioned and I remember the day as being one of the hottest ever. I watched him walk over to the registration desk and chat with the clerk behind the desk. After some pleasantries, he handed Roger a key and he headed back to me.

"Was that your friend?" I asked.

"What friend?" he said looking at me like I had two heads. Then he quickly added, "Oh, yeah, that was him."

We headed for the elevator, climbed in and rode up to the floor the room was on. I think it was the 10th floor and remember thinking "Wow, this building is HUGE!" We got off the elevator and walked to our room, which Roger opened with the key.

Roger laid all of the clothes that he had bought for me and himself on one of the beds.

"Why don't you go take a shower," he said pointing to the bathroom. "If we need to return these we don't want them to be all sweaty."

"That makes sense," I said to him, "but I didn't bring a towel or any soap." (Can you tell this was my first time out of my little town yet?)

He took my hand, led me into the bathroom and pointed to the various items that any well-stocked bathroom would have.

"When you finish, just wrap a towel around yourself and come out and we will try on these clothes," he said leaving me in the bathroom.

When I had finished, I did as I was told and walked back into the bedroom. Roger was sitting watching the television.

"That was fast," he said. Then turning to the TV he said "Twins and White Sox, who do you like?"

"Gotta like the Sox," I said.

"Well, go ahead and watch the game," he said as he unbuttoned his shirt. "I'm going to take a quick shower. I mixed another drink for you." With that, he pulled off his shirt, pulled down his pants and headed bare-ass towards the bathroom.

Now, I had seen naked boys in the showers at school, but three things hit me immediately. First, Roger wore no underwear. Everyone wore underwear, usually the white brief kind. But Roger had nothing on under his pants.

The second thing was his tan. Being from San Diego you would expect him to have a tan and he did. The difference was that he had it all over his body. At summer's end when the boys were showering in the school gym, everyone had a tan either from playing ball all day or working in the fields. But we all had big ol' white butts. But not Roger. You could not tell the difference in tan from his shoulders to his butt.

Finally, I was surprised at the size of his penis. All of us kids in school had about the same size penis. It was the standard issue two- to three- inch variety that when excited got to five, maybe six inches. Roger's penis was easily six inches just hanging between his legs from a patch of dark pubic hair.

So, without another word, Roger left me sitting in the bedroom, sipping my rum and Coke and pondering how they do things out in San Diego. In a few minutes Roger came out of the shower with a towel wrapped around him.

"Can I ask you a question?" I asked.

"Sure" Roger replied shutting the TV off.

"Well… how come you don't wear underwear?"

"Why should I?" Roger replied. "Is there a law saying that all men must wear underwear?"

I chuckled, realizing that it had probably been a stupid question anyway.

"It's just more comfortable, that's why." Roger continued. "A lot of people don't wear underwear, well, at least in California."

"Can I ask you another question," I said hesitantly knowing this one could be more stupid than the first. "Why isn't your butt white like everyone else's? It's all tanned like the rest of you."

"Well," Roger explained, "there are beaches around San Diego where you can take all of your clothes off and no one minds. That way you get that 'all over' tan."

"Even girls?" I asked incredulously.

"Girls, guys," he continued. "No one cares. You know, there are a lot of things that we do in California that people don't do elsewhere."

"Oh," was all that came out of my mouth. My thoughts went back to the shed and the Playboy magazine. Women like that walking around with no clothes on, right in front of you. It would be like heaven.

When I came back to reality, I thought about my last question and started to ask it.

"Why is your…. Never mind" I had thought better of asking even though the rum had lowered my inhibitions.

Roger walked over to the bed and sat next to me. "What is it you wanted to ask," he said looking me right n the eyes.

"I… I… I wanted to know why your wiener is so long." There, I had said it. It was none of my business but I asked anyway. And not only that, after being treated so nicely by a really cool guy, I called his penis a 'wiener'. I turned red with embarrassment. Roger picked up on it immediately.

"That's OK," he said. "I'm sure it's not the first 'wiener' you've seen."

The way he said 'wiener' made me laugh and put me a little more at ease.

"Everyone's different," he said. "Some people are bigger, some smaller. How big is yours?"

I looked down and for the first time realized that the thoughts of Playboy and naked girls strolling past me on the beach had given me an erection.

"Oh," Roger said with a smile. "Your's is pretty big, too."

"Mine's really smaller, it just that I… er… well, you know."

"Sure I do." With that, he unwrapped his towel and reached for his penis. Slowly he stroked up and down its length until it started to stiffen and stick out from his body.

"There," he said looking at it proudly. "That's what happens when I get stiff. Now there's nothing to be embarrassed about, is there?"

I guess there wasn't. I was fascinated watching him stroke his ever-lengthening member and by doing so my own penis hardened even more.

"Well, let me see yours," he said feigning impatience.

I don't know if it was the rum or whether I admired him so much that I would do anything for him, but I pulled back the towel and exposed myself to Roger.

"Very nice," he said. "Nothing to be embarrassed about."

I still had not taken my eyes off his swollen organ and had become more fascinated with it. The head had blossomed like a mushroom and the sides ran with thick veins. The shaft disappeared into a thick bush of pubic hair and his scrotum hung loosely below.

Roger watched me watch his hand. Although I had said nothing for about 15 seconds, it seemed like an eternity. Finally with a hushed, almost breathless voice, Roger broke the silence.

"Do you want to touch it?"

"I don't want to be called a 'fag'" I replied. (Apologies to my gay friends, it was the vernacular at the time.)

"You wont. Like I said, we do a lot of things in California that aren't done out here. Do you want to?" he asked again.

I did not answer. I had a buzz going from finishing my third rum and Coke and just stared rudely at his penis.

Without another word, Roger took my hand, moved it to his penis, wrapped my fingers around it and guided my hand up and down his shaft.

"Feels nice, doesn't it?" he asked quietly. All I could do is nod.

He reached over and wrapped two fingers around my own hard penis and stroked it slowly. I closed my eyes and the two of us stroked each other without a word spoken. The air conditioner hummed in the background bathing us in cool air, but it still felt like I was on fire.

I felt him lean over and his lips brushed against mine. I knew I should have said something, done something, anything, but I didn't and my lack of reaction signaled Roger that I had not minded his advances.

He leaned over again and placed his lips on mine this time lingering and gently sucking my lip into his mouth. Then, he moved and placed a kiss on my cheek, on my neck and finally in my ear where he whispered "You feel good."

Again, I did not, could not, answer. My heart raced in my chest and my head spun between lust and sensibility. Never having experienced the first, the second had little or no chance. My hand was on autopilot, moving up and down his shaft, feeling every bump, ridge and vein ending either in his bush or at the head of his penis.

He whispered again into my ear. "Tell me if you want me to stop."

I opened my mouth but nothing came out. Nothing came out because I didn't know what I wanted to say.

Roger's lips traced back down my neck and across my chest, lingering at my nipple. He sucked on it and lightly bit at it creating goose bumps all over my body. Lower he slid until his head was right over my penis which he still held in his hand. The next thing I felt was his tongue on the tip of my penis. I had been aware of my pre-cum bubbling up from inside me. As Roger's fingers had reached the top of my shaft, they would wipe the pre-cum off the top and bring it back down my shaft. Now, his tongue was licking the droplets off the tip.

As he lowered his head on to the shaft, he slid off the bed and his penis fell from my hand. I wanted to reach down and hold it again but before I could his mouth enveloped my organ. My hands went to his head and held it, not sure if I wanted him to continue, not sure if he had to stop. Be he did continue and started sucking the head of my penis and then sliding the entire organ into his mouth.

He buried his face in my pubic hair and then slid back up the shaft only leaving the head in his mouth. Then without pause, his mouth slid back down and my penis disappeared into his mouth.

Roger continued this for what was probably five minutes, but it seemed like five seconds. When he stopped he lifted his head and looked me in the eyes. He could tell that there was something between us. It was probably just lust, but it was there.

He brought his lips back to mine and kissed me gently.

"Would you do that for me?" he asked.

I nodded. No words were spoken for I could not speak. He simply stood up in front of me with his penis hanging in front of me. It seemed so strange to me, so foreign. It was something that I had never done yet seemed so natural. I leaned forward and took him in my mouth. There was no taste, no smell save for perfumed hotel soap.

Roger took my head in his hands and guided me up and down his shaft. At first, I just opened my mouth and let his penis slide in and out but after a few minutes I wrapped my lips around his shaft and formed an oral pussy for him. He slid his penis back and forth careful not to push too far into my throat. To be sure, he took my hand and wrapped it around his shaft so that the back and forth motion included a hand job also.

Without warning he tensed, pumped a couple of times more and shot his sperm into my mouth. I had tasted my own on occasion and was not put off by his action. For some probably perverse reason, I was proud that I had helped him cum.

Roger dropped to his knees, took my face in his hands and kissed me deep on the lips. His tongue twirled around the saliva and cum in my mouth and then he again took me in his mouth. With the skill of an expert, he gave me a blowjob that to this day had never been equaled. Maybe because it was my first. Maybe because it was him. But for whatever reason, I exploded into his mouth and had an orgasm that I will never forget.

We lay back on the bed knowing that we had hours before we needed to catch the train. For an hour we lay together with the only movement being my hand stroking his penis. We blew each other again before we packed up and headed for the train station.

We rode back on the train in silence, rode home in his car and when he dropped me off he simply said "Happy Birthday."

Six days later he was headed back to San Diego and for 30 years the memory of that birthday gift stayed with me as my sole homosexual experience.

Fast forward twenty years.

When I was 18, I had been seduced into performing oral sex on a friend and it stayed with me as a ghost or a treasure depending on how you view it. I did not consider myself gay or bisexual. If you jump out of a plane once you don't consider yourself a skydiver. If you hunted once and liked it but never did it again, you were not a hunter. Neither was I gay or bisexual.

To the contrary, I had several girlfriends and was finally married at 25. I produced a daughter who, knock on wood, is well adjusted and smart. But after 12 years, the marriage sort of disintegrated when my wife found someone she liked better. She liked him better because he was around, unlike me whose job kept me on the road sometimes weeks at a time. So, at 37 I was free to play the field and managed to have a couple of brief relationships with women my age. They were looking for someone to be more committed; I was looking to get laid so it was not a good fit.

So, here I am a year later at 38 sitting in the lobby of a hotel in Washington DC. It is a nice hotel that caters to both tourists and business travelers, me being the later. The manager puts on an "open house" where from 5:00 to 7:00, drinks are free. Of course the beer does not have a "born on" date since if it did it would be collecting social security and the mixed drinks are, well, drinks only in name.

I got there at 6:00 and the place was already jumping. OK, it wasn't jumping, just packed with the "free booze" crowd. I grabbed a beer and scouted out a table in the smoking section and managed to grab the last one. It had four seats and I am sure it would have been nice for a party of four to use it, but first come first served. I opened my planner and started reviewing my itinerary for the next day when a man and woman came over to my table.

"Would you mind if we joined you?" the man asked. "There doesn't seem to be any smoking tables left."

Knowing how much I enjoyed a cigarette with a cold beer (even a stale one) and not wanting to rob anyone of that simple pleasure, I simply pointed to the chairs and said "Not at all."

They turned out to be Rob and his wife, Liz. Rob was about 50, maybe a little older. He was almost completely bald but still fairly handsome and in good shape. Liz's face put her at early 40's but possibly more. Her body was tight and thin and could have passed as being that of someone 10 years younger.

I simply introduced myself as Bill Walters and we chatted for a while about why we were in town and what our plans were. They were staying at the hotel also. As we got close to finishing our drinks, Liz turned to Rob and said, "Honey, why don't you get us some more drinks."

Rob excused himself and left me alone with Liz, who leaned over the table and started speaking quietly so as not to be overhead by neighboring tables.

"Bill, do you like excitement?" she asked.

"Yeah, I guess so," I answered, not sure where this was headed.

"Bill, Rob and I saw you sitting here and were hoping that you might be interested in something." Without waiting for an answer she continued.

"Bill, I like to watch Rob suck on another man's cock and to get fucked up the ass. We were hoping that you could be the 'other man' tonight."

You could have knocked me over with a feather. Here I am sitting nursing a cold beer minding my own business when I get a proposition like that. When I had regained some composure I looked back across the table at Liz.

"I don't mind getting sucked on by a guy," I said making it sound like it was an everyday occurrence, " but I don't think I would go as far as fucking him. And I certainly don't want to suck him or have him fuck me."

Report Story

byCourtStJester© 3 comments/ 31464 views/ 1 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel