I was a pretty normal teenage jock. Women, sports, and partying were my priorities. Like nearly everyone I knew, I was generally repulsed by the thought of two men doing anything together sexually. I had certainly never been attracted to men in my life.
In fact, the summer after high school was spent in pursuit of girls. I was lifeguarding and teaching swimming at a private club.
Part of the day was spent fielding the advances of Jewish mothers who wanted to make sure their daughters got to play before they started husband hunting – or who wanted to play themselves while their husbands were off making more money. I certainly didn’t mind the opportunities, and most of these girls were attractive, and nearly all had great bodies. Some wanted to learn about sex, and some wanted to practice what they knew. I was willing to help them all.
One particularly eventful day began with the typical preparation for the swimmers and sunbathers. It soon took a turn when a particularly attractive mother-daughter pair began competing for my attentions. Their offers became progressively more suggestive and direct, and I was having a hard time deciding just what I might want to do. When mom could take it no longer, she finally offered that she would be willing to share me if her daughter was interested. Not being sure if they were serious, or if I was being set up, I headed for the pump room when my shift on the chair was done.
The pump room was a nice haven for the guards, since it was underground, out of the sun, generally cooler than the deck, and there were no people to watch – or watch out for. Walking in out of the bright sun, my eyes adjusted enough to check the dials on the filters and insure that all was normal. Letting my thoughts roam, I began to imagine both of those attractive females working on me simultaneously. It wasn’t long before I had a raging hard-on that wasn’t going anywhere soon. I couldn’t very well go back up on deck like that, so I pulled my cock out of my trunks and began to work it. Within minutes, thinking of a mother lovingly teaching her daughter new skills on my body, I exploded all over the wall. A few minutes to compose myself, and I was back up on deck.
After closing the pool that day, the head lifeguard came over and asked if I wanted to go for a ride. We had done this once or twice, usually going to get a beer and catching a quick buzz to wind down after the day in the sun. After being out for a few minutes, with thoughts beginning to mellow, he said he had a confession. He had watched me down in the pump room. He was in a far corner making a repair when I had come down earlier. He said he didn’t notice me when I came in, because of the noise from the pumps, and didn’t say anything once I began playing with myself. He let it die at that, and we finished our beers and headed back to the club to leave for the day.
At the end of a summer of working and getting ready for school, I left for college. After I had been there a while, I invited my lifeguard friend to come visit, since he wanted to get to the mountains and we had spent some time partying on a few occasions after work. He was considerably older than me (I was 18, he was 29), but we had gotten along fairly well for the entire summer. Most of the time we spent together was spent partying. I was planning a big party at school, and needed him to bring some supplies from the city.
He showed up, and his first night visiting we had a lot of people at the party (partying was fast becoming my top priority), including my girlfriend. Throughout the night, I introduced people to him so he would feel more comfortable – and thinking he might get lucky with one of the girls who had come on to me. The night wore on, people gradually left, and I crashed on my bed while the remains of the party continued around me.
Suddenly, someone was someone pounding on my door. There was a warm body against my back, but this wasn’t too unusual since my girlfriend spent most nights with me. I realized that there was an arm around my waist, and a hand on my erection. Half awake, I thought I should pursue this when I got rid of whoever was at the door. Except I realized that the hand wasn’t my girlfriend’s. I could hear her at the door – she was the one trying to get in. Shocked, I realized it was him, but my shock still didn’t keep me from taking my time about getting up. I told myself that I didn’t want to embarrass either one of us by waking him up while he was laying like that, except that he then asked who was at the door as he lightly squeezed my cock – to let me know that it wasn’t a mistake on his part. I went and opened the door after composing myself. My girlfriend came in, yelled at us both for locking her out, and made sure everyone was okay – then we resumed the party.
Nothing else happened during his visit. We ignored that episode, and wrote it off to the effects of the night before. Later in the year, when I had to make a trip back home, I stayed at his place out of convenience. After traveling all day, when I got there I needed to clean up. A few minutes into my shower, I was surprised by him walking in. He pulled the curtain back, claiming to check on me, but I noticed that he took his time looking at my body. I got offended and asked him to leave. After he walked out, I realized I liked it enough to have gotten a hard-on in the process! I dried off and went in to recover from the flight, and promptly fell asleep.
I woke up to the sensation of someone going down on me, and looked down to see him. I was scared, shocked, surprised, and angry that he would do this. Then I remembered. He hadn’t said he had seen me masturbating during the summer, he said he had watched. He asked if I wanted him to stop, and I realized I loved it, and said no. He was passionate about giving head. He continually looked up at me to make sure I was watching him work. I was quickly getting over my anger, and my revulsion at a guy touching me. More than that, I was quickly getting hooked on the idea of being serviced by a guy. He continued until I was ready to explode. Feeling me holding back, he looked at me again and sucked and stroked harder. Pushing me over the edge, he kept going until he had swallowed every drop. I realized then that he was more of a head guard than I had known!
I realized I didn’t have to hide that I had enjoyed it, the results were obvious. Wiping the little bit of cum he had missed from the corner of his mouth, he moved up to straddle my chest. I wasn’t sure what he had in mind, but was too satisfied to worry. He then started stroking his hard-on just inches in front of my face. He asked me if I liked watching him jerk off. I had to admit it excited me. He asked me if I wanted him to come. I said he could if he wanted. He clarified that he wanted to know if I wanted him to come on my face, and told me to close my eyes when I said yes. In seconds, he worked himself to orgasm. There wasn’t any doubt from my side when he got there – I began feeling his warm, sticky cum landing on my face. Cheeks, eyes, nose, chin; they were all recipients. What I still remember though, is when it first landed on my lips. I couldn’t help licking them. I tasted warm, wet, salty, and something new. I liked it.
Surprisingly gently, he began wiping my face. I didn’t feel ready to get cleaned up. Feeling that hot come on my face had pushed me over the edge. I grabbed his cock before it had time to get soft and eagerly started licking it. I wasn’t sure what I was doing, or how I should be doing it, but I knew I wanted to feel his cock – and feel it in my mouth. Apparently I had skills I hadn’t known of, because I’m not sure which of us liked that more, but the first time I ever touched a man, I took all of him into my mouth. I sucked and licked like a natural until he told me he was going to come. He tried to pull away, but I realized I didn’t want him to. I kept going until I had swallowed every last drop!
Now I was just getting hornier. In a matter of minutes I had gotten head from a man for the first time, watched another guy masturbate (and felt the results on my face), sucked my first cock, swallowed my first load, and I wanted more! He was clearly enjoying this turn of events too, for he was back between my legs about to start on me with his tongue. I looked at him as he took my rapidly growing penis in his mouth, and asked him to fuck me. Despite the startled look on his face, he went right to work. He was quite patient, especially considering how incredibly horny he was. He gradually touched me more intimately; starting by simply touching me in places I had never been touched. He licked my asshole, pressing the tip of his tongue in just a bit. He tried to slide it in, but I was much too tight. I felt him pull away and realized that I didn’t want him to stop those sensations!
I soon realized that I had nothing to worry about. He was right back, and began working some lubricant around when suddenly I felt his fingertip inside me. While I was in amazement that he was actually doing that, he slid his entire finger in. I reflexively tightened, and we had to work for some time for me to get relaxed enough to enjoy the sensation. He asked how it felt. I told him I never expected it to feel like this. When I began moving against the thrusts of his finger, he asked if I still wanted him to fuck me. I answered that I did, so he slid his finger out and lubricated his now very-stiff cock. Straddling my prone body, he pressed the tip against me, and was pressing gently (I don’t know how, because we were both insanely horny) when I rose up and back to get him inside me. My body tightened at this new invasion, out of pure reflex, but he was inside me.
It took a bit for me to relax, but once I did I was in ecstasy. He was behind me, moving slowly, and reached around my waist to lift me up on all fours–when he started stroking my cock while he fucked my ass. I thought I was going to come apart from all of the sensations I was feeling. And I nearly did. He kept pumping, sliding his cock repeatedly in and out, getting both of us more and more excited. With him jerking me off while he was fucking me, we were both getting dangerously close to exploding. He told me he was ready, and started to pull out. I reached back to grab him, and made him stay inside me. When I began to feel his cock spasm in my ass, I began to come with him.
I fell back asleep that afternoon, but the next couple of days were pure abandon. At one point, his roommate walked into the living room as we were lying on the sofa, him reaching around me from behind, stroking me. His roommate simply paused on the way through to let us know he was home. Needless to say, my fear and hesitation were over.
We met discreetly on occasion over the next two years, and had great sex every time. On the next encounter he hungrily took me into his mouth on a hill overlooking the city, bringing me to a great orgasm (which I enjoyed quite selfishly). When we returned to his apartment, he started on me again. This time, however, I wanted to try more. I moved him up onto the bed, and straddled his face as he promptly went to work with his lips again. But I also went to work on him. I quickly had him rock-hard, rolling his head around on my tongue. I had to know, and wanted to experience it, so I decided I was going to try to take all of him into my mouth and throat. I did so, easily. It certainly wasn’t that he was small; rather it felt like something I had been doing all of my life! I made the decision that I didn’t want the distraction of him sucking me, so I moved around away from his eager mouth. I felt like the biggest cock-hound around, but I wanted him so crazy he was fucking my mouth hard. I think the combination of my lips on the base of his shaft and my throat on the head of his cock was far more than he had planned for. He began thrusting his hips to my face, and getting ready to come. When he was about to explode, he tried to pull away. I grabbed his ass firmly, feeling his pelvis pressing against my mouth. He looked down at me with his dick in my mouth and told me he was going to come. I simply grinned, nodded, and kept sucking.
As he began to shoot I pulled back just a bit, so that I could feel that warm wet load in my mouth. I just kept bobbing and swallowing until he was spent, then began sucking like he was a drinking straw in my favorite dessert (which was pretty accurate at that point). Then I moved up to straddle his chest, and began working my erection. Just as I was about to lose control, he leaned forward and shoved me into his mouth. Before I came, he pulled back, and had me turn around on his chest. Thinking that he wanted a good angle to take all of me in again, I began to position myself to that he could. Before I got there, I felt his tongue start to work on my asshole. Within seconds, he had it inside me. As soon as I felt that, I exploded. All over his stomach and my chest.
He kept working his tongue, fucking me with it. In minutes, I noticed that he was getting hard again. I hated to waste such a good combination – his stiff dick, and my ass lubricated and relaxed. I flipped around before he could argue, and sat down on his cock, sliding it inside me as I went. The look on his face was priceless, since he hadn’t been prepared to be fucking me so suddenly. I’m not sure who was fucking whom, since he was thrusting up and I was doing my best to keep him moving deep inside me. At any rate, he came. Hard. And we slept.
The last time we saw each other, we had gone to a baseball game. We stopped by his apartment on his way to drop me off. While I was sitting at the dining room table, he dropped to his knees and began to give me one of his great blowjobs. He asked if I had enough time to move into the bedroom. I simply went. Within minutes we were naked, and competing for each other’s erection. We actually managed to maintain our session of 69 until we both came at nearly the same time. Then he asked if he could fuck me. I turned around, giving him clear access to my ass. By now I knew all too well just how good this felt, so there was little effort required for him to get inside me. He spent several minutes with his hands on my hips, delivering long slow thrusts inside me, pulling me back toward him as he did so. When he reached around me to start stroking me, I knew he was close to orgasm. I took his hands off of my cock and put them on my shoulders as I told him I wanted to feel his entire load in me. He obliged, shooting it all and continuing to pump until he slipped out.
I expected him to rest for a few minutes, but he quickly pushed me onto my back and went down on me hungrily. No eye contact, no hesitation, he just wanted my cock in his mouth and he wanted to taste/feel me explode there. I did. I loved the way he sucked dick. When he finished, he sat up and said he had a favor to ask. Puzzled, I wondered what it could be, since we had always just done whatever we were thinking about. He said he was trying to figure out where his relationship with his girlfriend was going (oh yes, there had always been girlfriends and women between our encounters). He said he wasn’t sure if he was gay, or bi, or straight. I pointed out that our escapades could rule out the last!
He got serious as he waited for me to stop joking, and prepared his next question. “Would YOU fuck ME?” Oh. I loved his cock, and the sex we had, and getting fucked by him – even though it didn’t happen often – and the passionate way he gave head. I liked feeling my lips on his erections, tasting him come, the feel of his dick in my hands. I had come to enjoy seeing him above me trying to hold off as long as possible until I saw him begin to explode all over me, and I enjoyed masturbating for him, on him. I knew I liked every aspect of him fucking me – the way he pulled me toward him, or the feel of his hands reaching around me to stroke me while he was inside me. I knew if I did this, and he liked it, things would change between us. It wouldn’t be casual anymore. There would be expectations, and disappointments. I decided then that I would rather live with the remembered pleasure, and walked away.