Rediscovering My Friend

The story I'm about to relate is technically my first time with another man. I say that because, when I was younger and learning about my body, I had a friend who liked to experiment as well.

And, happily, he later became the first man I had sex with in the more literal sense.

To start, my friend Jim and I have been best friends since we were in grade school. We did everything together growing up - riding bikes, reading and swapping comics, going to the town swimming pool, sleeping over at each other's house. As we got older, we even double-dated.

But, between the time we were playing with our 'Star Wars' action figures and the time we started to go out with girls, we were curious about the changes in our bodies. We 'borrowed' our older brothers' Playboy and Penthouse magazines and went off to his or my basement to see what was what.

A few years later, we 'discovered' real girls as opposed to the two-dimensional kind. And, by the time we were seniors, we were lucky enough to both lose our cherries. With the same girl but at different times.

College came along and we ended up going to different schools. I stayed near St. Louis while Jim went to California. We saw each other at breaks and over the summer but only spoke occasionally during the year.

The second summer we were home, we were going out to hang with some friends. On the way, he seemed edgy and asked if I'd drive around for a while. He seemed to want to talk but, knowing Jim, it might take time to come out. I asked but didn't pressure him, he'd tell me when he was ready. We were close enough that there were never any real secrets between us anyway.

Finally, he told me he wasn't a virgin any longer. I looked at him, wondering what he was talking about. I knew that. I knew the girl he'd fucked the first time. When he finally explained, I felt a bit like a moron. He hemmed and hawed for a while then finally told me he'd slept with a man. And it was not a one-time thing. I found myself pulling over to stare at him.

He turned pale and mumbled something. I asked what and he said, "I guess we aren't friends anymore."

I hugged him and said that was ridiculous. He was more like a brother to me than my own brother. Then I asked him about what had happened.

As he told me, with only the barest of details, what happened I realized I wasn't surprised. But, deep inside, I had to admit to myself that I was disappointed his first time wasn't with me. When I realized that, I was dumbstruck once again.

The rest of that summer, and the summers and breaks that followed, were pretty uneventful. We got together, hung out by ourselves and with our friends, went to concerts and movies - the usual stuff. Jim's new lifestyle - he had eventually told me that women just weren't exciting to him anymore but men were - never really came up.

Well, except for the moment he told his parents. While they were initially upset, they came to realize Jim was still the same loving son they had raised. Fortunately, his parents, while good Catholics like mine, aren't too narrow-minded. They came to accept his alternative lifestyle. And pretty quickly too.

After college, we both ended up working in different parts of the country. I was lucky enough to stay close to home and got my own apartment. Jim ended up in the New York area - Long Island specifically. We stayed in touch by phone and he visited often enough that it was still kinda like our college years.

And I admitted my fascination of male sex - to myself. I would go to bookstores in the Central West End and buy magazines with pictures and stories in them. These became a major source for my solo sexual escapades. (I wasn't ready to go to adult shops for gay videos - that was more than I had the courage to try at that point. And the internet wasn't quite as 'sophisticated' as it is now.)

I never explored that aspect of my life outside of very personal, very secret fantasies. Neither Jim, my folks, Jim's folks, my girlfriends, or anyone else would've suspected my lurid dreams.

Finally, I made what I thought was a big mistake when Jim was home for a visit. We were in a bar and I had just enough to drink that I mentioned it to him. And the fact that I often had the image of Pete (his college lover whose picture I'd seen once) with his dick up Jim's ass. As soon as I said it, I regretted it.

Fortunately we were in a semi-private booth and no one else heard me. Jim had, of course, but didn't say anything for the longest time. Finally he asked me why I'd waited so long to tell him. I admitted I was scared - scared of my feelings and desires and scared of society's attitude.

Turned out he was upset because he had just started a relationship with a man he'd met in NYC and it was developing well. He asked me, "If I'd asked you last year to have sex, would you?"

I told him yes but then seeing how that seemed to hurt, I added, "I think so. I'm not sure. It's all so new."

We talked long into the night about this. He admitted he wanted to have sex with me but he couldn't while he was involved with Steve, his new lover. I agreed and said I wouldn't either while I was involved with Becky - a girl I'd been seeing for a couple of months. After that, the subject never really came up again during his visit.

A few years ago, during one of our long-distance phone conversations, Jim asked me if I wanted to try something new. I agreed and we began to have phone sex a couple of times a month.

The first time, we arranged a time to do it and I was lying on my bed, naked when he called. The pattern repeated with Jim or I doing the calling after pre-arranging a convenient time for both of us.

The first few times, we told each other stories - fantasies. My favorite was telling him what I pictured him doing the first time. It had become pretty involved considering how little he actually told me about how Pete had seduced him. He enjoyed telling me about the first man he seduced. These and other stories were more exciting than anything in any magazine and I came every time. And I came a lot.

Soon, we began to describe what we'd do to the other as we stroked ourselves. This was just as hot, if not hotter, and we always seemed to experience orgasms at virtually the same time. Just hearing him moaning and breathing as he climaxed would get me off and I'd end up moaning with him.

We also used private email accounts to share stories, links, and images. Soon, I was sitting up at my computer, masturbating with my best friend as we shared the same gay sites on the web. While not as comfortable as laying in bed, it was very exciting to be looking at the same pictures or reading the same stories while we jerked off.

More than once, I'd come so hard, I ended up having to clean the monitor.

A year or so later, Jim began to plan a trip home the following summer - his first since we had begun our long-distance trysts. We discussed this and what it would mean to see each other in person for the first time since we began long-distance sex. We agreed that we would not allow it to interfere with our friendship regardless of our fantasies and long-distance jerk-off sessions.

The possibilities were there for us now that both of us were single again. He'd broken up with Steve about the same time Becky and I had split. In my case, it had nothing to do with Jim but was just the gradual withdrawal in a relationship that wasn't meant to be. (I later learned the same happened between Jim and Steve which was a huge relief to me. I never want to come between anyone if I can help it.)

Jim sent me a short email a month after he told me he was coming home. He said he still wanted to experiment with me. If I wasn't interested, it wasn't going to be a problem. But, if I was, to let him know. Boy did I let him know! This is practically a direct quote from my response: "HELL YES I WANT TO EXPERIMENT!"

We both got blood tests to assure each other we were clean (something we both knew but we wanted the confirmation before we did anything). We both took them, got the results, emailed them to each other and did a follow-up test before he arrived. Fortunately, neither of us was interested in anyone else at the time so sex - with someone else - was not a factor.

Since I no longer live in our home town, Jim agreed to stay with me and we wouldn't tell his parents or anyone else he was in town for the first few days, regardless of what happened.

The Thursday before Memorial Day, I left work and drove to pick him up at Lambert Airport. I arranged to take the next day off so we could hang out together for a long weekend before he went to see his parents.

I met him at the airport baggage claim - as far as I could go into the terminal at Lambert due to the new security demands. We hugged and I swore I felt a spark of something. We grabbed his two bags and headed to the parking garage for my car.

On the way, I looked him over. I caught him doing the same. He seemed to be pleased with what he saw as well. I know I was.

Neither one of us were weight-lifters, not by any stretch. But we did keep in good shape by judicious use of local gyms - running, swimming, and bicycling.

I have to say Jim was in excellent shape. His hair, always lighter in color than mine, was lightened further by the late spring sun (he was always practically blonde by the end of the summer) and his skin was lightly tanned. The golf shirt he wore was snug without being tight and the cargo short he wore cupped his ass nicely.

We got to my place and I showed him to the spare bedroom. We had decided to take it easy and not force anything. I was still nervous about actually having gay sex and Jim was nervous about having sex with me.

After getting settled, we headed out for an early dinner then back to the apartment. As with the drive from the airport, we spent the time getting caught up. But we were both still checking each other out as well.

Once we were back home, I headed to the bathroom and took a shower. I wanted to be squeaky clean inside and out for Jim. Just thinking about it made me stiffen. While I had never put anything bigger than two fingers in my ass, I wanted to be ready just in case. I thoroughly soaped myself and found I was getting harder as I washed then rinsed my anus. As I hadn't masturbated in over a week, my hard-on was difficult to ignore. But I managed to.

I threw on some jogging shorts and a light, pull-over shirt after yelling into the living room that the bathroom was free. Soon, I heard the water running and got hard again.

Sitting in the living room as I waited for my oldest friend to come out, I was suddenly extremely nervous. I wasn't sure I could go through with anything at all. I mean, I was about to have gay sex! With my best friend! And dwelling on it seemed to make the anxiety worse.

When the shower shut off, my body jerked. I kept glancing nervously towards the hallway leading to the bedrooms. Then I'd look out the window at the creeping dusk. Then back to the hall.

An eternity seemed to pass by, eventually, when Jim came out wearing a tight pair of shorts and a cut-off t-shirt showing off his flat stomach. His hair was still damp from the shower and he looked...incredibly sexy.

As he sat next to me, I felt the nervousness slowly fade. He asked if I was okay and I told him how nervous I had been. He put his hand on my knee, the heat swam right up to my crotch, and asked, "Are you sure you want to do this?"

I could only nod. He gently squeezed my leg as he leaned in. His breath was warm on my cheek as his lips came near me. Such lovely kissable lips. It seemed amazing I had never noticed how sexy his lips were before.

And they were soft too.

As we kissed, I felt a thrill course through my body. It was like the airport but much stronger. I opened my lips slightly and felt the tip of Jim's tongue caress them. Then, the softness slipped into my mouth to caress my tongue. His tongue retreated and mine followed into his mouth. He tasted sweet, like mint toothpaste. And I loved it!

We lost ourselves in this kiss. Our tongues slipped and slid along each other, caressing and feeling. All sense of time was gone, only the reality of the kiss.

When we pulled apart, my shorts had tightened as had Jim's. No kiss had ever excited me as much as that one did. When I pulled back and looked in Jim's eyes, I saw my own excitement reflected there but I also saw something else. Not quite fear but worry, like maybe he'd gone too far.

I smiled, cupped his face in my hands, I had to find out if it was just this one time... My fingertips stroked his cheeks as I leaned in and kissed him. Just like the first time, it was soft then wet then... It was everything.

We sat on my sofa trading kisses for quite some time. The kisses were often soft with closed lips. They were just as often soft with tongues intertwining. And then there were the more passionate, wetter kisses. Every time we broke a kiss and paused, one of us would look at the other and the kissing would resume. It was like neither of us could get enough of the other.

While we kissed, our hands roamed each other's upper body. I ran my fingertips over his flat stomach, slipping a fingertip into his navel. He pulled my shirt up and teased my nipples with his fingers. We shivered at the sensations, those shivers shared through our kisses.

By the time we finally took a break - Jim actually had to get up and step away - the sky outside was dark and I could see the moon beginning to rise over the office tower across the way.

I touched my lips, marveling at the experience while wondering how long we had kissed. Never had I been so lost in the simple act of kissing. Not that all of our kisses could be considered simple. Passionate and full of meaning and desire yes, but simple - no way!

Jim reached down, taking my hand, and pulled me to my feet. As I stood, he pulled me into a tight embrace and kissed me again, his tongue snaking into my mouth.

My hands slid around his bare stomach, holding him close by the waist. His hands slid along my back, feeling me through the thin cotton.

I could feel him straining against his shorts, the taut bulge rubbing my equally hard bulge. I felt like I could come just from the sensations I was experiencing. When he slid one hand down under my shorts to caress my ass, I moaned loudly.

I pulled back and said, "I... Slow down, Jim."

He looked at me with care and concern, "Am I going too fast? Do you want to stop?"

"No!" I practically shouted my response. "No, don't stop. I'm loving this. It's just... We might want to slow down some or I'm gonna come right here."

His hand, which was still cupping my asscheek, squeezed me as he smiled. "Then we better take care of that..."

He dropped to his knees and yanked my shorts down to pool at my feet. My dick slapped him lightly on his cheek, leaving a gleaming drop of pre-cum. Gently taking me in hand, he looked at it with what I took to be admiration.

I am not some superstud with a foot-long penis. I'm probably about average - a little over seven inches and a bit more than an inch around when I'm aroused. Not huge but more than enough for Jim, I hoped.

He licked his lips and said, "I'm going to take care of this little problem and then we can take our time..." With that, he swallowed my shaft!

The wet heat was incredible. When his tongue caressed my shaft, my knees got weak. He pulled back until the only the head was in his mouth. His tongue laved it and pressed the slit - I didn't know whether to moan in ecstasy or giggle at the tingly feeling that also came. I did both.

Jim's tongue covered every centimeter of my cockhead, always returning to the bottom, licking the cleft. Then he bobbed back down, taking practically the whole thing in his mouth.

He pulled and looked up with a smile. "Better than I imagined," he whispered before taking me into his mouth again.

Then the world turned white and I lost it. Without thinking about it, I leaned forward and balanced myself on Jim's shoulders as I climaxed. Dimly, through the waves of pleasure, I felt his mouth moving as he swallowed my cum. That prolonged the exciting feelings, the thought that my oldest friend was swallowing my seed.

Jim released me and stood up. He smiled at me, asking, "How was it?"

I shook my head. I couldn't find any words. Instead, I grabbed him by the back of the head and pulled him to me for more kissing.

I could taste myself in his mouth. It was better than when I had tasted my cum after masturbating. I kissed his mouth, his cheek (licking up the dollop of pre-cum there) and all over his face. Jim giggled and said, "I guess you liked it..."

Finally I managed to say, "What about you?"

"Are you ready?"

I nodded. I wasn't before but at that moment I wanted nothing more than to bring my best friend to a roaring climax. "I have to have you. In my mouth... in me."

"Let's get comfortable," Jim said. He took my hand and led me to my bedroom and to my bed. He pulled my shirt off, leaving me naked. He looked up and down with a pleased smile and then said, "Take my clothes off."

I knelt down and reached for the waistband of his shorts. I stopped and grabbed the ragged edge of his shirt, pulling that up and over his head. Tossing it aside, I kissed him again. I seemed never to get enough of those kisses.

I again knelt before him and tugged at his shorts. His dick, which had softened a bit, came into view. It was perfect, nestled in his patch of pubic hair with two beautiful balls hanging close at the base. It was familiar and different at the same time. Familiar since we had spent so much time playing with each other as kids. But it was different too. When we were kids, he had a thatch of pubic hair over his dick but no hair on his balls. Now, he still had curly hair around the base of this magnificent cock and on his balls as well.

He kicked the shorts away and I gently took him in hand. He stiffened almost immediately. Like Jim had with me, I admired his equipment for a long moment. Then I licked the drop of pre-cum that had formed at the tip. It was delicious: salty and creamy. And I wanted more.

I looked up and apologized, "I don't know exactly what to do so..."

Jim smiled - he has a beautiful smile - and told me, "Don't worry. I am so excited to be with you that it won't matter. Just do what you like having done." I nodded and opened my mouth when he added, with a chuckle, "Just watch the teeth."

I giggled and decided to start with some tongue action. I licked the shaft from the base to the head, feeling the warmth of him. Up one side and down another. Then I licked the head again, wrapping my tongue around the sexily spongy tissue.

Jim moaned and ran his fingers through my hair. I licked the slit, tasting more pre-cum. He shivered as my tongue touched him. I traced down the large vein along the underside to his balls and back up with my tongue.

Then it was time to take the plunge. I opened wide and took him into my mouth. The solid shaft felt so right between my lips. Using my tongue, and concentrating on keeping my teeth away, I sucked and bobbed on his cock. One hand lightly caressed his balls while my other hand reached back and slid up and down the crack between his cheeks.

He pulled me back, saying, "I'm going to come."

I nodded, "I know. I want you to. In my mouth."

He nodded his gratitude as he pushed me back over his shaft. A few more sucks and he came. Boy, did he come!

I pulled back a bit so only the head was in my mouth. Then I felt the first couple of bursts hit the back of my mouth. After several warm blasts, the remaining cum flowed onto my tongue in small pulses. He was salty and wonderful. I loved it! I wanted more! So I continued to suck, hoping to coax more from his beautiful cock.