My First Time

I am a divorced man in my late 50's and very, very confused about my sexuality. I have been married and divorced 3 times and my sex life in all of the marriages was not exciting but primarily used for procreation. I don't know – perhaps I subconsciously looked for women with a low libido so I wouldn't have to perform too often. In all three cases, the sexual interests of my wives dropped to almost nil after a year or so and we tottered on in matrimony for several more years until calling it quits. In each case, fighting against some inner demons, I sought another partner within a couple of years and repeated the process all over again.

Something very deep inside me was nagging at me but I fought it tooth and nail since I was a teenager. I was always small for my age and somewhat effeminate in both looks and demeanor and, as such, suffered as the butt of jokes and teasing from both boys and girls. Because I was so shy and didn't show any interest in girls (I was too petrified of rejection so would never ask one out), I was often called a faggot or a queer. Of course, this only served to increase my sense of shame and eroded any ego I might have had.

When I went away to college, I lost most of my acne and grew over 6" in as many months so although I was still very shy, I was able to lose myself in my work and became quite a success with high grades. I was even sought out as a tutor for some of the jocks (to keep their athletic scholarships) and the occasional female who was in jeopardy of losing her parent's financial support if they didn't keep their grades up. Just being in the company of those my age without incurring their scorn was a growing experience.

Of all the athletes I worked with, John Turner from the basketball team had an unsettling effect on me. Every time we sat side by side in either the library (or occasionally in his dorm room), I could feel butterflies in my stomach and would rush back to my dorm room (I lived in one of the few single rooms in the residence) and masturbate excitedly. I was frightened as I realized it was images of John that ran through my mind as I stroked myself to a shattering climax; why wasn't it one of the cheerleaders or another good looking co-ed? What was wrong with me? I couldn't be a fag, could I?

So much for history. After the three failed marriages and as I neared the end of my fifth decade, I acquired a computer, took some lessons and tried my hand at the internet. It wasn't long until I was receiving pop-up ads inviting me to join pornographic sites. Now, of course, I had acquired explicit magazines over the years – always, it seemed to involve gay men or, if couples, I always was mesmerized by the men's' cocks. However, the explicit sites (many of them free) blew my mind. Perhaps this was my way to meet a man and explore my hidden desires?

After about 3 months of wondering through the net, I discovered a chat room site strictly for men. I joined and posted a profile with a code name "curious". It took me a while to figure out how to use the message board and I often just sat there watching the messages stream across my screen. Then, one evening, a message popped up. "Hey, curious; why do you never talk? This is supposed to be an interactive site, not just to look at"

It caught me so off guard, I almost missed it; the sender was named "lovingman"

I timidly responded replying that this was my first time online (I realized they knew better having seen my name when I signed in) and I was unsure of exactly what I wanted and why I was even here.

Lovingman "no reason to be afraid; we are all the same here"

Curious "But I have never been with a man; just think I need to find out something..."

Lovingman "so what is it u need to know?"

Curious "there is so much and I only know that I am not happy the way I am"

I was given directions on how to enter a private chat room with lovingman and after a few clicks of the mouse; we were the only ones there.

Lovingman "so, babe. Tell me your story"

I was taken aback by his familiarity but it had been so long and this seemed anonymous enough, so I proceeded to pour out my life to this complete stranger. It took almost three hours of my typing and his encouragement until I had fully unloaded my crappy life onto his shoulders.

As he started to tell me more about himself, I found that he was a 55 year old man who lived about five hundred miles or so from me and had led a not dissimilar life. He had been married and divorced twice and his current wife was not sexual at all. He had been using the chat room as an outlet for his sexual frustrations for two years now and occasionally wrote erotic stories for an online site. All his stories were about his fantasies of having sex with another man although he claimed he had only tried it twice – neither time was all that satisfying. I asked him to direct me to the site and he supplied me with the .url and his pen name.

I glanced at the clock and realized it was almost midnight – we had been chatting for four and a half hours and I had to work in the morning as did he. We promised to meet online the next evening (his wife worked 12 hour shifts at the local hospital in the evenings from 7:00 pm so he had all the time in the world to chat).

As soon as I could, I rushed home from work, grabbed a snack and went online to read his stories. He had 17 posted stories about man to man sex and I found myself so aroused, I jacked off three times as I read them. At 7:30 a message popped up on my screen: "lovingman" is calling.

I wiped the last of the cum off my cock as I clicked on the box to open our private chat room. I couldn't type fast enough to tell him how much his stories had turned me on! After I told him I had stroked myself to three climaxes in an hour and a half – more than I had ever been able to do before – he asked me if I would like to experiment with some online sex and masturbate together. I asked him if he was sure that no one else could read what we were doing and he assured me that in the private chat room no one would mind – it happened all the time.

We stripped all our clothes off and spent the next three hours describing to each other what we were doing. It was the most exciting evening I had ever had and we continued this online 'affair' for the next three months only missing those days his wife was off.

As we became more and more intimate online, we started to talk about exchanging pictures - both clothed and nude. I realized that pictures could be faked but we went ahead anyway; I used my digital camera to take a couple of pictures and after receiving his (he was as described – graying hair, about 189 lbs, strong jaw hairless body and a nice cut cock perhaps 7" long and thin like mine). After he got my shots (white hair and beard closely trimmed, 175 lbs, also hairless and as I said, similar cocks), we became even more turned on.

I screwed up my courage and finally asked him if he would be interested in meeting somewhere and sometime. He readily agreed and we decided to take some time to find a place and date that would accommodate a day or two for exploring our fantasies. I had some weeks of unused vacation due me and so did he. Since he was into fishing, he often went off on trips to the North Country with his buddies and his wife could care less.

So out plan was hatched; we found a town about a four hour drive for both of us that was on an isolated lake. There were cabins for rent with all the modern conveniences and, since this was the off season, I easily secured a place. In fact, we were the only ones there and the owner who lived in a nearby town said he would leave the key under the door mat. After sending in a security deposit equal to the rent for the three days, we both set off although not without some trepidation. We agreed to meet enroute in a small city about an hour from the lake to have lunch in a neutral location just in case we didn't hit it off or the pictures lied. We both agreed on who would bring what in the way of food, drinks, etc.

As I nervously sat at a back booth in the small diner - I always arrive early for appointments - awaiting lovingman (I knew his name was Sam and I am Bob), I scanned the parking lot until I saw a small SUV pull into the almost empty lot. It was Sam and he looked exactly as his pictures had shown but in person, he seemed to loom larger then life. As he entered the diner, his eyes were drawn to me immediately and a wide grin lit up his face. He was as pleased as I was!

He sat down across from me and since there were a few other patrons in the room, we exchanged handshakes as jolts of electricity shot through us both. When our knees touched under the small table, I felt my cock twitching in anticipation and I leaned over the table before the waitress came to tell Sam the effect he was having on me. His only words filled my heart with happiness "Me too!"

Lunch seemed to fly by as we rubbed our legs together under the table and occasionally brushed hands together as we reached for the condiments at the same time. In no time, it was over and, paying the bill, we walked around the building out of sight and Sam gathered me into his arms and his lips descended on mine hungrily. "I have been waiting to do that for months" he said huskily. "Now let's find that cabin before I ravish you here!"

My legs were shaking as I climbed into my car and led Sam's SUV to the lake in the warm sunny afternoon using the directions the owner had provided. All the time, my hand was rubbing my bulging crouch where my cock was straining against my jeans; that kiss had set me on fire. Suddenly my cell phone rang; I picked it up and heard Sam on the line.

"How much further? I have my cock out of my pants and it's dripping with precum for you to clean off!"

I almost drove off the road as I told him about my own arousal and advised him to hold on – it was only another mile or so until we reached the turnoff. I hung up and sped up before I came in my pants from the excitement. I realized that the front of my jeans was stained right through with my own precum; I must have been streaming it since that kiss!

I turned into the lane to the cabin and madly drove to the end until I reached a clearing by a small peaceful lake. The setting was beautiful – just right for my first tryst with another man. There was not another soul in sight. Before Sam had stopped his SUV in a cloud of dust, I grabbed my grocery bags out of the trunk and ran to unlock the door. I ran into the rustic interior and threw the perishables and drinks I had bought into the running fridge and turned as Sam came dashing in behind me with his bags.

"Get your stuff into the fridge only as needed! Hurry up! I can't wait much longer!" I cried as I started to undress myself.

"Slow down" he laughed. "This first time is going to be slow and easy and I want to make it last for both of us"

I could have loved him for that; I stopped my eager fingers and walked over to help him unload our food and drinks. We each grabbed a beer and went outside to sit side by side on the swinging lounge on the deck overlooking the lake. All we could hear, aside from our own breathing, was the occasional call of a loon across the lake.

"Perfect" we said in unison, leading us both to laugh.

We put our bottles on the deck after only a sip or two and, turning towards each other, gently kissed. It was unlike any kiss I had experienced in my experiences with women; I suppose a man knows exactly how he wants to be kissed and the sharing of this intimate gesture was the 'thing' I had lived my life looking for.

Our kisses deepened and became more and more arousing; both of were breathing raggedly and we finally had to come up for air. Breaking the kiss, we rose together and walked into the small bedroom that was almost filled with the big bed. As I stood there uncertain what to do, Sam started to unbutton his flannel shirt and tossed it aside; man, I loved the smoothness of his well-defined chest and I ran my fingers lightly across it and as I brushed his nipples, they hardened immediately.

Hurriedly now, Sam undid his belt, kicked off his sandals and shucked his jeans. Moving to me in only his much tented briefs – I could see the dark stain of precum filling the front and the glistening of it as it ran down his leg – he slowly unbuttoned my shirt trailing kisses along each exposed part of me in so doing. My legs were trembling (partly in arousal, partly in fear of what would happen and if I could please him).

Sam sensed my nervousness and, after shedding my shirt, pulled me into his arms to renew the kisses we had already shared. As our bare chests rubbed together, I felt my nipples rubbing against his and they grew hard sending jolts of aroused energy to my now hard cock. I reached impatiently for the waistband of Sam's shorts and ran my hands down his backside to cup a pair of very firm buttocks. I pulled him into me to feel our cocks rub together even through the rough material of my jeans and we groaned in unison.

I stood away and quickly doffed my clothes to stand naked as his jockey shorts hit the floor. It was almost like looking in the mirror (except for the weight difference) and we moved quickly to the bed and crawled into each other's arms. As we rolled back and forth – kissing deeply all the time – we kept exchanging positions. I would lie on top and then him. Whatever the position, our cum-slick bodies were rubbing against each other until we started breathing heavily. We were too close too fast!

We moved without a word into a 69 whilst lying on our sides and carefully examined up close our first real cocks – well, mine in any case. As I cradled the weight of the warm pulsating shaft in my hand and breathed in the manly aroma, my head spun as my tongue tentatively reached out to touch the urethra that was oozing precum. I had tasted my own juices but this was so different. It was tangy and musky at the same time and I loved it! I lapped up and swallowed every drop of the ever increasing stream (always holding it on my tongue to savor the flavor). If his precum tasted this good, I could hardly wait to taste his cum.

Meanwhile, Sam was way ahead of me as I felt his warm mouth engulf my full 7" and his hands cupping my full balls. God, I was going to cum in his mouth and I hadn't even tasted my first cock yet! I quickly remedied the situation by opening my mouth as wide as I could and slid it over the dome of his deep red glans. In my inexperience, my teeth grazed him and he freed my cock from its heavenly embrace long enough to warn me to cover my teeth with my lips if possible. He then retuned to dive on my cock and hum his way to the bottom. I felt it hit the back of his throat and I reciprocated – managing only about 6" before my gag reflex took control.

However, I wanted to give him the pleasure I was receiving so I pulled away to take a breath, relaxed my throat and this time I found that it was relatively easy. Even though I had to take more breaths than Sam, we were soon in a matched rhythm as we sucked and stroked in unison.

After months of anticipation, we both knew that our first time would be quick and it was! It couldn't have been more than 10 minutes of these ministrations on each other and we were both moaning around the other's cock as we tried to warn of the impending explosion. However, neither of us was prepared to stop or withdraw and with a minor swelling of the cock in my mouth and the feel of Sam's balls rising – I wonder if he feels the same of mine – I came with a mind blowing climax and emptied a huge load followed by several others into Sam's throat. As I felt his muscles swallowing around me, my own mouth was filled to overflowing with the sweetest taste in the world – Sam's cum!

I did my best to swallow it all but it was simply too much. I have never cum that much myself in my life and I continued to take it in, taste it on my tongue and feel the warmth of it sliding down my throat. Much still spilled down my chin onto Sam's thigh and I greedily licked it clean.

I could feel him licking my cock clean so I followed suit. He was, as was I, huskily moaning with the pleasure of the experience and we returned to each other's arms and kissed deeply, sharing the taste of each other. The meld of flavors – so different and yet so much the same – was amazing and we held tightly to each other after pulling a light blanket over ourselves and fell into a deep sleep.

What might the rest of the time bring!