My Cumming Out

In the mid 1970’s I finished my time in the Navy and returned to San Francisco to start my college years. The gay scene was hopping in the Castro but being kind of a shy young man I was not in to the bar scene or social life. My focus was on school and work and being able to afford to live in San Francisco.

The first problem was finding a place to live. I had had it with group living and got out of the dorms as quickly as possible. My solution was to rent a small apartment from a couple of nice older guys in lower Pacific Heights. It was a safe neighborhood, close to school and work and was cozy and cheap. Little did I know that the two 50’s something guys, Bill and Al, would become far more than landlords and upstairs neighbors. In the back of my mind I sensed they were a gay couple but in those days gay couples of that generation kept to themselves and lived as “room mates” and were not open about their orientation or living arrangements. I just figured they were a monogamous couple, quiet and nice, and left it at that.

Being 24, blond, in super shape and tanned from running distances on the beaches I was quite a target for the older crowd but being shy I faded away from most hook ups and stayed to myself. Bill and Al regularly talked with me as I came and went to work and school and occasionally made little passes, cute quips about my butt or hairless, trim body. The kept coaxing me up to their two story part of the house under the pretenses of getting me “out of the basement” but I shied away. Over time they wore men down and one night on the offer of some beer and food I went up to their apartment.

Bill was bolder than Al and once at their apartment and after my second beer I had to pee. I went to the bathroom and squatted to pee. As I was draining Bill came in the bathroom, looked down at me and said “you are one cute little chicken.” He then laughed and said “don’t worry, Al and I won’t let anything happen to you. Our house has always been a safe place for young gay guys, we have each other, and we just want to have smart young friends who will tease the hell out of our regular running partners.” He then went on to tell me that if I ever wanted a blow job or was horny they would take care of me and save me a trip to a bar or cruising cottage.

I pulled my shorts up, and as we walked out of the bathroom and back in to the living room Al notice Bill following close behind me and then winked at me as Bill pinched my ass. Flustered and intimidated I blushed and kind of froze, and then I felt Bill’s hand gently cup my ass cheek and he whispered to me “don’t worry, we won’t bite. Suck like hell, but won’t bite.” Both of them burst out laughing and I nervously joined in.

For the next few hours we had beer and food and talked and they had their hands on me in gentle ways. At about 10 Bill put his hand over my hard tool and asked me if it was time to take care of that swelling. I was speechless but did not resist as my running shorts fell below my knees and exposed my tool. Bill gently held it by the shaft and directed my glans to his mouth. At that point it was all over for me and my celibate lifestyle!

Both Bill and Al took turns on me, gently working on my cock and holding my shaft and balls firmly as they milked me. After five minutes I could not hold on any longer and I exploded in Al’s waiting mouth. He kept my cock in his mouth, clamped his lips around my shaft and worked my glans with his tongue as I pulsed hot semen in to his throat. He kept going and then passed me off to Bill who did the same. He pushed me back on the couch and kept working my cock until I started getting hard again, and ever so gently he slipped a finger up my ass and on to my prostate. Gently massaging my walnut and working my glans he brought me back to full erection. This time they both took turns on me, sucking and working my cock aggressively and massaging my prostate with first one and eventually three fully inserted fingers. Once again at full erection they found my sensitive spot under my pee hole and worked it and my prostate until I exploded again. I slumped back in to the sofa and let out a groan. At that point of total surrender both Bill and Al sat close next to me, hands all over me, and whispered in my ear the details of the new reality I was entering.

That night they proposed and I agreed that we would have a “family night” two or three nights a week. Those nights were determined by my school schedule and work but would be hard commitments. I would come up to their place, fully charged, and they would cook healthy food, we would have beer and wine and then they would drain me.

So for the next 4 years every Tuesday, Thursday and Sunday night I went to their place and we did our ritual. Over time they gently introduced me to receiving anal sex from both of them after my first draining. They expanded my sexual horizons slowly and gently over time and eventually these family nights became more of a three way gang bang. They would bring in a third out of their many friends so I would leave their place fully drained of my own baby batter but pounded and flooded full of semen from two or three of them. We became close friends and I got very close to their group of friends. My end of the bargain was to live free in their house, be available and willing and also be helpful around the place. That fit my budget and sexual needs perfectly. I guess I became the original rent boy at that point.

For nearly four years my sexual needs and energies were consumed with this arrangement. I was getting my brains fucked out three times a week. Both men were careful about who they brought in to our little group and many were straight married guys they knew from work. So unrestrained bareback sex was the rule of the day for me and I got used to being full of semen all of the time. On the days and nights in between they might come to me for a quick blow job or fuck so I was really never in a position to go hunting for sex. I had all I could handle.

Bill and Al also brought me out as far as the club scene and fetish scene in the Castro. We would go as a threesome and meet their friends at the clubs. They jealously guarded me but did so for my own good. There were a lot of chicken hawks out there who were bad news for a young, impressionable bottom like me. They kept me on a tight leash and safe and for that I am forever grateful.

After I graduated and left the City I did return occasionally. They had brought in another young rent boy and I got used to that idea. We remained close friends until both passed away in the late 1990’s. I guess they set me on my path of always being attracted to older, masculine take charge types. I had the best sex of my life with those two and the best friendship as well.

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