tagGay MaleA Bisexual Summer of 1959

A Bisexual Summer of 1959



We were in our regular rendezvous location outside the church in an alcove shielded by high bushes. There was tree behind the shrubs as well and at that moment Gilbert had both hands on the trunk. He was leaning over holding onto the tree with his back arched emphasizing the shape of his curvy bottom. His pants and underwear were down around his knees and his shirt was pushed up clear of his buttocks.

I was behind him with my pants and briefs around my knees. My 7" cock was buried in his lovely ass. I caressed and held to the hairless, flawless, smooth buns as I sawed my cock in and out of the snug passage. I was enamored with the scrumptious ass and pleased to be fucking it again. The anal sex began a couple of weeks ago. At first, I was worried about trying it but now I looked forward to it.

It was nearly 9:00 PM and we were concealed by the darkness and the tall bushes. My eyes had adjusted and I could see my cock sliding in and out between the magnificent globes. Gilbert had a great looking ass and I knew many girls who would have loved to have his shapely bottom. We had only been fucking for about 15 minutes but I was getting close; his ass did that to me. Sensing that I was close he whispered.

"Cum on my ass."

He liked it when I came on his ass especially with my first load as it was usually massive. I felt that familiar tingle and surge, so I pulled out and ejaculated onto his lovely bottom. Gilbert was rapidly stroking his cock and then he too ejaculated, his seed landing on the ground. I put my cock back in his ass and let him milk it with his sphincter. That action drained my shaft but also kept me hard. I was able to fuck him a second time and that time, I came in his rectum.

Using a handkerchief, I wiped my dick clean and wiped my seed off of his sweet cheeks. We pulled up our underwear and pants and redressed. He turned to look at me and smiled. He had a cute face and even though he was 20 and I was 18, he looked younger than me. We left the church grounds and walked together for a few blocks before we would separate and go our own way home. Before we separated he asked.

"My parents are gone this weekend. Do you want to come over on Saturday?"

My girlfriend and her family were still on vacation so I agreed. "Sure, I'd like that."

"Come over after lunch, my parents are leaving in the morning."

He told me his address as I had never been to his house. I recognized the street name and I knew that he lived in a very nice neighborhood.

"Okay, I'll be over after lunch."

"I'm looking forward to being totally naked with you."

I had not thought of that but we had never been naked. We were always in our clothes whether he was sucking my cock or I was fucking him. All the times we had sex, our pants and underwear were around our knees. He said good night and headed off in a different direction. My house was nearly 2 miles from the church grounds and an easy walk. On my way home, I thought about the upcoming Saturday and I was looking forward to it.


I am Wally and I had just graduated from high school in June 1959. At 18 years of age, I stand at 6'1" and weigh a chiseled 185 pounds. I have light brown hair and hazel eyes. In high school, I lettered in three sports and remained fit. I dated one girl my senior year and she was also 18. Susan was a cute brunette with dark brown hair that she wore in a DA style. She was 5'6" with tiny tits and a nice ass. We never really had sex per se, it was only mutual masturbation. I fingered her pussy and she jerked me off.

There were other girls who put out and I could have fucked them or had them blow me. However, they all had big mouths and I knew that it would get back to Susan. I really liked her and enjoyed dating her, so I didn't want to screw that up. She and her family, younger sister and parents, always took a summer vacation together. They had left mid-June and would not be back until sometime in August. One Saturday night, I decided to walk into town and go to the local movie house.

It was a movie with Marilyn Monroe, the blonde bombshell. She was wearing a very tight dress that showed off her voluptuous body. She would give any normal guy a hard-on. The theater wasn't very crowded as in those days, the same movie ran for weeks. I was sitting about three seats off the aisle when this guy plopped down in the seat next to me. I was surprised since there were plenty of other seats.

I looked at him and he had a cute face and appeared to be younger than me. He started making gestures and whispering about Marilyn. As she moved around on the screen, he uttered phrases that I found to be funny.

"Oh, look at that ass. Oh, those tits, I would love to put my face between them."

Since it wasn't crowded and the utterances were whispered, only I heard them. He had me laughing at his behavior. That went on through the entire movie and he even rubbed his crotch a few times. He was almost entertaining. The movie ended and we walked out of the theater together. He introduced himself as Gilbert. He was 5'6" and slender, in fact somewhat effeminate. As we walked together he told me that he was home from college. I was impressed to hear that he attended Oxford in England. Within two blocks he changed the topic to sex.

"When I get home tonight, I going to jerk off thinking about that babe."

I laughed again. "Do you have a girlfriend?" he asked.

"Yes, but she and her family are on vacation. That's why I went to the movie by myself."

"Do you have sex with her?"

"Not really, well kind of, we masturbate each other."

"Really, she doesn't blow you?"

"No, she doesn't"

"Have you ever had a blow job?"

"No, I could from other girls at school but they would shoot off their mouths. I'm sure things will change when I'm in college."

"Yeas you're correct there. At Oxford guys are wanking, sucking cock and fucking all the time."

It was clear that he was telling me that guys were doing it. He then asked me to walk to the church with him that he had something he wanted to show me. I was a little leery but also curious. Since I was bigger and obviously stronger than him, I wasn't scared. We went to the church building and then ducked in behind the bushes. He moved close to me and ran his hand over my crotch.

"Hey, what are you doing."

"Relax, don't worry I'm not going to hurt you."

I knew he wasn't going to hurt me, if anyone got hurt it would be him. He continued to run his hand up and down over my crotch. Whether I was horny because Susan was gone or from watching the movie, I got hard in my pants. The sensation of his rubbing my crotch was enticing. I didn't even realize that he had managed to pull my zipper down. His hand moved inside my pants and rubbed my crotch through my cotton briefs. I felt like I might cum at any second. When he unbuckled my belt and unfastened my pants, I panicked a bit.

"Don't be scared, let me make you feel good."

He pushed my pants down to my knees and then pulled my briefs down to meet them. My 7" boner sprung out and bobbed in front of my pubes. He wrapped his around the shaft and stroked it slowly. It was only the third hand to ever touch my cock, Susan's, mine and now his.

"You have a great cock. Do you jerk off a lot?"

"Sometimes at home."

"Three times a week when you're not with you girlfriend."

"Maybe, at least twice."

"Can you cum multiple times?"

"Yes, always twice, sometimes three, even four once."

I recalled the day that Susan jerked me off twice and then at home that night I got off two more times thinking about her. Gilbert would occasionally spit on his hand and then return to stroking my cock. It felt good and at that moment I thought why not. Who would know if some homo jerked me off? I was not expecting or prepared for the next move.

Gilbert leaned over and took my cock in his mouth. It felt fantastic as he mouthed my shaft and licked it up and down. He fondled my testicles and rubbed the perineum, driving me wild. My balls were bloated and I thought I would explode at any moment. Gilbert was an excellent cock sucker and he had me ready to cum. He took his mouth off my throbbing dick and whispered.

"Let me know when you are ready to shoot."

"I'm really close."

He did not take it back in his mouth but resumed stroking it. I warned him that I was going to cum. He continued jerking me off and I shot six forceful streams onto to the ground. The first two spurts traveled two feet. He kept stroking me until I stopped shooting and then took my dick back in his mouth. He sucked me dry and I remained hard. Lifting his mouth off of my cock, he spoke softly.

"I had a feeling it would be a big load. I didn't want to swallow that much cum. You're staying hard, can you go again."


He took my cock back in his mouth and sucked it until I came a second time. This time he let me cum in his mouth and it felt wonderful. He sucked me dry and then we were done for the evening. I sheepishly pulled up my briefs and pants to redress. I suddenly felt embarrassed about the encounter. We left the church grounds and walked together for a few blocks. He asked me to meet him by the church again on Wednesday evening about 9:00 PM.

I agreed to meet him even though I wasn't sure if I would. I was still feeling odd about the oral sex even though it was fantastic. That night in my own bed I jerked off twice, thinking about the blow jobs. It was then that I knew, I would show up on Wednesday.


I used all my will power not to masturbate Sunday through Tuesday as I wanted to be ready for Wednesday. I left my parents' house telling them that I was going to the soda shop. I arrive at the church a little before nine and Gilbert was there waiting. He smiled at me and then we ducked behind the bushes as we had done the first time. This time he wasted no time and he had my pants and underwear down to my knees.

He used his oral skills to perfection and within minutes I was ready to cum. As he did they first time, he stroked my cock and watched me shoot. Again, it was a massive load and he smiled and remarked.

"My, my, look at it all."

Then he took it back in his mouth and sucked it dry keeping me hard. I was surprised when he stood up and shocked when he lowered his pants and underwear. His small erection popped out and I guessed his cock was about five inches. I had no interest in reciprocating and I made that clear.

"Gilbert, I not going to suck your cock. I don't do that."

"I know, I want you to fuck me. I want to feel that beauty in my ass. I want to feel you shooting in me."

"I haven't fucked anyone, you know that."

"I know, It's easy. I'm going to put some cream on your dick and my anus. You always want to use some cream."

He took a small tube out of his pocket and squirted the cream on my shaft, he stroked it briefly spreading the cream around. Then I watched as he fingered his anus and put the cream there as well. He leaned over and held to the tree. Arching his back, he wiggled his shapely ass at me and encouraged me to enter him. I was overcome with lust and I did as he directed.

"Use a steady pressure to get the head in and then go slowly. Not too deep at first and then deeper."

I moved the spongy mushroom head to the rubbery ring and pressed forward. The head opened the aperture and disappeared inside. I could feel the snugness and I pushed ever so slowly. Little by little I went deeper. Each time backing out just leaving the head in and then feeding him a little more cock. I was really getting into it now and fucking my first ass was an incredible experience. I loved watching my cock move in and out between his scrumptious ass cheeks.

His ass was hairless, the skin was flawless, not a mark om it. The buttocks were super smooth and I liked feeling them in my hands. I caressed and squeezed them as I drilled his ass. It was the most exciting thing in my life at that moment to be fucking a super fine ass, even though it was a guy. Suddenly, I felt that familiar sensation that I was felt right before I ejaculated.

"I'm going to cum."

"Good, stay in my ass. Cum in my ass, I want to feel it."

My toes tingled and curled inside my shoes. The ball sac tightened and I unleashed a huge load into his rectum. There was a gripping and contracting sensation around my shaft as my dick was spurting. Gilbert was stroking his cock rapidly and soon he was shooting on the ground again. I stayed in him, stroking his buns, until my cock softened and slipped from the chamber. I stepped back and starred at the marvelous ass that I had just fucked. It was still unbelievable how good it felt.

"So how was it? Did you like your first ass fuck? Do you like fucking me."

"It was great. Yes, I liked fucking you. I never thought I could do something like that but it was really wonderful."

"Good, I'm glad you liked it. We'll do it again soon."

Gilbert took a handkerchief out and placed it at his anus. I watched as my semen trickled out and he caught it in the cloth. We both pulled our pants and underwear up and redressed as always. Once again, we walked together for a few blocks and then went our own way. At home that night I jerked off twice thinking about the anal sex and his lovely ass.


We continued to hook up at the church but increased the times we got together. He would always blow me first and then I would fuck him. He gave great blow jobs and his ass was fantastic. Although, I could never suck cock or take it in the ass, I loved being with him. Then the Saturday rolled around when I was to meet him at his house.

I arrived at the house and admired it. I had driven through the neighborhood a few times and was always impressed with the stately homes. Now I would be in one. Gilbert greeted me and invited me inside. He sensed that I was nervous and offered me a beer. We sat in the living room with our beers and he told me stories about Oxford.

I don't know if they were all true but they were erotic and put me at ease. He described his classmates as insatiable blokes who were wanking cocks, sucking cocks and fucking all the time. He described group sex with three and four students. Sometimes things got wild in the locker room and a regular orgy would break out.

"You would be a big hit with your big cock," he told me.

We finished our beers and went to his bedroom and undressed. It was the first time we both would be completely naked. Gilbert got in bed on all fours with his curvy butt stuck up in the air. I could feel a tingling in my loins as I looked at his hot ass. His body was delicate, hairless and flawless. He really did look like a girl in this position. He was tanned except for his ass and the contrast in skin color really emphasized the shape of his curvy ass. Up until then, I had only seen his ass when we fucked at the church.

"Wally, are you ready to fuck me?"

My cock was hardening and I approached the bed. I knelt behind him and I began to caress his beautiful ass. He handed me some lubricant and asked me to get his ass ready for my cock. I put an ample amount of lube in my hands and rubbed it all around the taut rubbery ring. Then I inserted first one finger then two fingers preparing him for my cock. This was the first time I was preparing him for my cock. As I sawed my fingers in and out of his anus I was getting turned on by the thought of burying my dick in his shapely ass. After greasing my shaft, I moved closer to him and lined up the head of my cock with his anal opening and began to ease it into to him.

"Take it slow at first, then deeper."

My cock head cleared his sphincter and I fed it to him a little at a time. His ass chute was warm and tight as I went deeper and deeper into him. Soon I was all the way in his ass and I started a slow fucking motion. I continued to pump him with deep, long, deliberate thrusts as I caressed his smooth round ass. He asked me to fuck him harder and quicker. So, I picked up the pace and I started pounding his ass faster and faster. He was moaning with each thrust of my cock. I could feel my release building and I knew that any moment I would shoot my seed in his ass. I tried to make it last as long as possible but the contractions around my shaft were too much.

I fired a barrage of cum in his ass filling it to overflowing. As I continued to fuck him, my juice backed up in his rectum and began to ooze out flowing over his balls. He used his talented sphincter muscle to milk my cock and drain it of all my seed. I didn't think that I would ever be soft again as I remained hard in his tight sheath. The milking action weakened me and I collapsed on top of his body. Gilbert flattened out on the bed with me on top and my cock still in his ass.

"Oh wow! You certainly know that you have someone on top of you when you're on me."

We moved to our sides and lay next to each other momentarily drained. I could see the bed sheets where Gilbert had shot his load sometime during our fuck session. We both relaxed and sometime during our rest my cock softened and slipped from his ass.

"I've been thinking about your cock for days," Gilbert rasped.

Gilbert next covered my cock with his mouth and gave me one of his mind-blowing blow jobs. He ran his hands over my body and up my body to my abs. He scraped his finger along my perineum causing me to shiver. He caressed my bloated balls and swirled his tongue around my cock. I gently grabbed his head as I knew I was close to cumming. Gilbert picked up the pace and he soon had me shooting my second load of the day down his throat. Cum shot into his mouth and Gilbert swallowed as quickly as he could so that he did not miss a single drop. He kept my cock in his mouth and drained every drop from my shaft. Next, he took my cock from his mouth and ran his tongue around the mushroom head and he caressed my tight ball sac. I was shaking from the tingling sensations as he nibbled gently on the head of my cock sending shock waves through my body.

Gilbert stroked his cock as he desired to achieve his own release. I watched as his hand moved rapidly over his cock and his ball sac tightened just before he ejaculated. I reached over and ran my hand over the ball sac touching him for the first time. He groaned when he felt my hand caress his balls and then I ran my finger under the sac and scraped his perineum with one finger. I continued to play with the ball sac and perineum until his body stiffened and cum shot out of his cock.

I watched as the first cum shots flew out and hit him on the neck, shoulders and chest. Some even landed on his face and hair. The next volleys landed on his ribs and abs. Gilbert moaned and groaned as he ejaculated and I kept rubbing his balls until he stopped cumming. The remainder of his seed trickled from his cock and puddled on his pubic hair. Gilbert lay still for quite some time before he composed himself enough to move.

"Come on, let's have another beer and recoup some."

We put on our underwear and got the beers. This time we returned to his bedroom with the beers. He told me more stories and showed me a magazine that he got in England. It was nude guys in different sex positions. All the guys were good looking and fit. I had never seen anything like it. The only nudie mag I had ever looked at was Playboy and that never had sex photos in it.

"Gilbert, I was surprised that you sucked my cock after it had been in your ass. Isn't that risky?"

"No, I had thoroughly douched and cleaned my ass before you arrived. Of course, you wouldn't know about that. I used my mother's douche."

We finished our beers and removed our underwear. He slid one hand across my belly wrapping his soft fingers around my shaft and pressed my cock up against my belly. Then I felt his mouth on my cock again. He caressed me with his tongue, moving from deep underneath my balls to the very tip of my cock in one lingering sweep. We both moaned as his tongue swirled around my swollen cock head, his hands caressed my shaft and balls. His fingers probed between my legs. He glanced up at me and then back at my cock before taking me deep into his mouth.

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