My First Gay Encounter

This is based on my experience over 40 years ago. It is my first submission to Literotica and I would love any and all comments. The names have been changed to protect the participants.

It all started in college. I went to a small college in the Midwest with just over 500 students. I became involved in a stage production of The Odd Couple and met Craig. He was a senior, handsome, blond, and a really sweet guy. He took me under his wing when we did the Odd Couple. He of course was Felix Unger and I played Vinnie one of the card players. Craig was a super dresser, work great cologne, and never had a hair out of place.

Craig introduced me to the chorus group and I also became a member of this wonderful group of students. Craig seemed to always be around and I never saw him with any of the female cast members of any of the productions I was in at college. I was advised by some of the female cast members to look at for Craig. It would be almost a year before I found out what they were talking about.

I attended the after show party for The Odd Couple at his house in the suburbs with one of the female cast members. I remember saying to Craig what a fabulous house you have and it was really decorated nicely. I think I was one of the few cast members to get a tour of the house.

It was in the spring of 1970 when Craig invited me to his house to open the pool. He had a large in-ground pool in his back yard. So I got a towel, Trunks and T-Shirt and headed out to Craig's place.

Craig answered the door in a t-shirt and white speedo swimsuit. He looked great. He had been working on his tan and we headed out to the pool and the lounge chairs. I went into the bathroom to change into my conservative swim trucks (Catalina) and he called in from the kitchen inquiring about wine. I said sure and we went out to the pool.

Craig immediately took off his shirt and I really got a look at him. I noticed he had very little body hair and the swim trunks really showed off his equipment. We sat in the lounge chairs and I sipped the white wine he provided. He suggested a dip in the pool to cool off. I took off my t-shirt and we both dove into the pool.

We both came up at about the same point in the pool.

Craig came up behind me and started touching my shoulders and neck. Next he was whispering in my ear and then he started tonguing it. It sent shivers down my spine. He then moved his hand around to my nipples and began to touch them. He spun me around and gave me the most sensuous kiss I had ever received from any one. Craig continued to rub my nipples and then it happened he slipped his hand inside my swimsuit and started to stroke my raging hard on.

Craig stopped and asked if I was okay. I said yes and then he suggested we take this in the house and get naked.

We toweled off on the pool deck and went into the house and sat on the couch after we took off our suits. I got my first look at his uncut cock. We continued out kissing and Craig started stroking my cock and then he took one of my nipples in his mouth and began to suck vigorously on it while pinching the others. He was stroking my cock and I reached out for his. We were stroking each other and then I came in his hand. It was wonderful. Craig asked me if I was okay and I said yes and I continued to stroke his cock. He kept giving me encouragement and I finally was able to bring him off in my hand. Craig suggested we clean up and go back to the pool.

We did not put our suits back on since it was only us and he had a privacy fence. We laid out at the pool and as the sun set I told him I was heading back for my apartment. I told him I needed to think about what just happened. He said he understood and then I got dressed. He walked me to the door with his arm around me and gave me another kiss prior to my leaving his house. Craig promised to call me and arrange another get together.

Taking the Next Step

About a week later Craig called and asked me I wanted to go out and have some Italian food. I agreed and he picked me up at my apartment. We chatted in the car and headed for dinner. It was great and Craig asked if I would like to go back to his place for a late night swim and I said I didn't bring a suit and he said we had been in the pool without suits before and we could do it again. I agreed and we put the top down on his MG and headed for the house.

As soon as were in the front door Craig took me in his arms and kissed me like no tomorrow. We were both tugging at each other clothes and I was rack hard in a matter of seconds. We placed out clothes on a chair and headed for the pool. WE got in and again began to kiss and cuddle. Craig knew how to push all of my buttons. He worked on my nipples and then did something to put me over the edge he started tonguing and kissing my arm pits.... I could not contain my self and started stroking his raging hard on. He kissed and twisted my nipples and then he placed me on the edge of the pool and started to suck my cock. This was something totally new to me and I went out of my mind. He also started fingering my anus. I was not sure where this was going but I did not want it to stop.

Craig was deep throating my cock and his mouth felt like heaven. He reached up and started pinching my nipples, my breathing became ragged and I told him to stop or I would come in his mouth. This only seemed to make Craig to suck faster and harder and to really pull on my nipples. At this point his finger hit something in my anus, he later explained it was my prostrate and I came gallons.

Craig came up and kissed me and we shared the cum in his mouth. This was hot and I hopped off the ledge and reached for his cock and started to suck on his nipples. I asked him if I could suck his cock and he said I did not have to he was fine with a hand job. I led him by his cock to the lounge chair and knelt next to my Adonis and just looked as his cock. I started by licking it from top to bottom and then I took the head in my mouth. It felt different and it tasted kind of funny as he was leaking a lot of pre-cum. I am sure I was not the best at cock sucking and once he told me to watch my teeth. I guess I made up for technique with enthusiasm. I stroked his cock with my hand and continued to vigorously suck his cock head. He told me to keep doing what I was doing and he was about to cum. He told me to take it out my mouth if I wanted and just continue to jack his cock. I was determined to get him to cum in my mouth. He did and a lot of his cum came out the corners of my mouth. He immediately lifted me up to sit on him and we started kissing and trading his cum. Craig broke the kiss off and said he needed to take me home, as he had to get to work in the morning. He did ask if we could go to a movie on Saturday. I immediately agreed. We kissed for a few more minutes and then we put our clothes on and Craig drove me home. We kissed in car at the entrance to my apartment. I reached over and squeezed his erection and then I jumped out of the car and went inside with a hand on. I went to bed and stroked my cock like crazy and thought about what had just happened and what was going to happen on Saturday.

Losing my virginity

Craig called on Friday to arrange a time and suggested I pack a bag and plan on spending the night on Saturday. Craig said I would not be needing much, as far as clothing went, just to pack a tooth brush. He suggested we have an early dinner and a movie.

Craig picked me up coming to the door. He stepped inside and we kissed passionately for a couple of minutes. Craig said we had to stop or we would never get dinner and a movie out of the way. We hopped into the car and went to a nice restaurant in an "artsy" part of the city. Over dinner Craig asked if I had ever been to an adult movie house. I said no and then Craig told me about he Olympic and what they on the marquee for tonight, Gay male movies. We had dessert and coffee and headed for the Olympic which was in this part of town.

Craig got tickets and we went inside. There were a few couples in the audience and a lot of solo men. We found seats and the movie started a couple of minutes after we sat down. Craig placed his hand on my lap and on the lump in my pants and I did the same. As the movie started we started to make out until the sex scene started. I watched the two men suck each other's cocks in a 69 position. I asked Craig if we could try this sometime and all I got was my cock squeezed. Then one of the men penetrated the others ass with his cock. I watched in utter fascination as Craig began to caress my nipples through my shirt. There was moaning on the screen and throughout the theater.

This was my first introduction to anal sex and I was really getting turned on and also the era of the beginning of "Money shots". The man took his cock out of his partners ass and proceeded to cum in his mouth. I told Craig I was a little worried about trying this. He whispered in my ear we would only do what I was comfortable with and he said he really enjoyed having a cock up his ass.

Craig continued to tongue my ear and stroke my cock and nipples. I told him I would cum if he continued so he unzipped my pants and pulled out my hard cock and started to stroke it harder. He told me to let know when I was close as he would swallow my load. I started to breath hard and told him I was really close and he took the head of my cock in his mouth and sucked me dry.

We then began passionate kissing and fondling for about ten minutes. We turned out attention back the screen and the next set of partners were in the missionary position with the man on the bottom having his legs over the shoulders of his partner who was slow stroking in and out of his ass. This time he came in the guys ass and then proceeded to eat the cum out of his ass. I really thought it was disgusting and told Craig I thought it was very gross. I was vigerously stroking Craig in his pants and got bold and pulled his cock out and stroked his foreskin over his cock head and told him how much I was enjoying the evening. I also said to let me know when he was close as I wanted him to cum in my mouth. He put his hand behind my head and towards the head of his cock. He fired a few ropes into my mouth and I managed to get most of it. We shared his cum and a kiss and Craig said we needed to take this back to his house and the bedroom. I agreed and we straighten our clothes out and headed out of the theater hand in hand.

We got to the car and shared a kiss prior to firing up the engine.

We pulled up to the house and Craig put his hand on my ass as we walked to the house. We continued into the house and Craig suggested we stop off in the kitchen for a glass of wine. We sat on the couch and kissed and sipped our wine as we slowly began to undress ourselves. We finished out wine and were naked when Craig stood up and reached out to me to lead me to his bed.

We got on the bed with both of us sporting erections. Craig suggested we try 69 as I had asked about it earlier. He told me to get on top so I could control the depth his cock in my mouth. We sucked each others cock for about 10 minutes and Craig started pushing his finger into my asshole and I did the same to him. He inserted a second finger and I followed what he as doing to me. He then did the most incredible thing he stuck his tongue in my ass. It felt strange and exciting. I did not stick my tongue in his ass. Craig asked me to get off him and then he reached into his nightstand and pulled out some KY jelly. He put a dollop on his finger and placed it on his ass hole and then he got some more and wrapped his hand around my cock and got it good and slippery. He pulled me too him and began a soul kiss I thought would make me cum. He guide my rock hard cock to his waiting ass hole and I proceeded to enter his ass. I tried to go slow but it was my first time and I think I may have been a little quick. He yelped on my initial assault, no pun intended. I would like to say I fucked him for an hour but I do not remember lasting but a few strokes before cumming in his ass. I must have shot a dozen ropes of cum in his ass and then collapsed on him. We kissed some more and my shrinking cock came out of his ass and we made a mess on the bed.

Craig got up and got a towel and wash cloth to clean himself, me, and to get most of the cum off the sheets. Craig now took control and rolled me on my back. He kissed me and fondled my nipples and began to work on my ass. He put some KY on his fingers and began to toy with my asshole. He got a couple of fingers in and hit my prostrate sending all kind of tingling through my body. He kept kissing me and eventually rolled on top of me. He asked me if I was okay and said yes and that I wanted to return the favor. He said I didn't have too so I grabbed the KY and lubed up his uncut cock and put some on my virgin asshole and Craig kissed me and slowly entered me. I cannot say it was not painful but when we was fully in my ass the pain surely turned to pleasure. Craig continued to kiss me and I began to pinch and pull on his nipples as he began to slow fuck me. A couple of times he came all the way out of my ass but was gentle when he returned. He began to pick up his pace as he got closer and then he really began to hammer me and told me to really pinch him nipples as he was almost there. He slammed his dick in my ass and came for about 30 seconds. We kissed and cuddled until he was soft and he pulled out of my ass and then got a wash cloth to again clean us both up.

We fell asleep in a spoon position with Craig's spent cock resting in the curve of my ass. I awoke to sunlight in the room and no Craig. I heard the shower running and had to pee so I went into the bathroom to relieve myself and Craig invited me to join him in the shower. I did and we soaped each other and kissed like men possessed. I bent down and took Craig's semi-erect cock in my mouth. I got about half of it in before it started to swell. Craig pulled me up and turned off the water. We toweled off and headed back for the bed.

We got into the 69 position and proceeded to suck each others cock. I came first and then Craig pulled me off and got the KY. I knew what was coming and he slowly entered my sore asshole. This time we fucked for about 15 minutes when Craig said he wanted to do me n my hands and knees. I got on my hands and knees and this time Craig was not as gentle. I was already opened up and Craig had a need for release. He did reach around and stroked my now rock hard cock. He fucked me hard and long. I came in his hand and I think my ass muscles must have clenched his dick as he came almost immediately afterwards.

We got up and I cleaned my ass in the toilet and we put on swimsuits and ate breakfast. We laid out at the pool and took a short nap before we entered the pool to cool off. Craig swam up behind me and pulled my suit down my legs and thrust his cock into my ass. The water made some lubrication but it was a little tough at first. He grabbed my nipples and began to bite my ears and neck. He was dicking me long and hard and moaning in my ear how great it felt to be fucking my hot ass. He came in my ass and pulled out almost immediately. The cum leaked out of my ass into the pool. I was rock hard and told Craig it was now his turn. I put him against the pool wall and placed the head of my cock at his ass. He reached back and put the head in his ass and backed up to me. I was surprised at how easily I entered him. I reached around and started tweaking his nipples and I too started nipping his ears and neck. I did last a little longer this time but not by much, I came hard and Craig turned around and we kissed for about 10 minutes.

We continued to lounge around the pool all afternoon before Craig decided to take me home. I did not know at the time this would be our only visit and I would never had another gay encounter. Craig got an offer to move to New York and started working in the theater. I was drafted soon after our encounter and we would never meet again.

The End