My Real First Time

Part 1

Like so many others before me I have struggled with trying to determine when it was that I discovered that I actually enjoyed and preferred sex with men. It probably wasn't during puberty and my budding adolescence when I got some interesting life lessons from a cousin or when my best friend and I used to spend many a summer evening skinny dipping in his pool and then jacking off together afterwards....I suspect it might not have even been when I was a member of the football and basketball team and I quickly developed an appreciation for how hot some guys looked in their jocks and in the showers......how cool it was that everybody was growing into their equipment so to speak....nope....not any of those experiences......Fast-Forward.........

I had completed my 4 years of college and had embarked on a path to heterosexual 'normalcy' (save one little drunken encounter with a guy in college) and had set out to save the world with two degrees - social work and political science and boy was I proud of that. I had taken a position in the adult world that afforded me to have the best of both of my worlds advocating and lobbying for public access to education - I even landed a position with a state legislator that let me run with the ball(s) so to speak - researching issues and developing legislation that would actually help people who couldn't afford to go to college get in.....

Fast forwarding again - my position allowed and actually required me to travel all over the state to meet, interview and interact with college students and people just entering the work force after college. Needless to say, many trips to cool cities with lots of attractive people, lots of nights out on the town, whichever that happened to be, but then lots of lonely nights in hotel rooms - Boy did I get an appreciation for being able to use both hands equally well!

I was, on this particular trip, in the southern portion of the state on a tour that would wind its way up the coast ending up in the north in an old school town with a very prestigious private university that was as old as the pines on its coast. My boredom at night caused me to start to experiment with the internet and various porn and sex sites and, eventually, being horny was a symptom of a bigger problem....I hadn't had sex in, well, I couldn't remember how long. My work was forcing me to spend a lot of time talking to and interacting with very attractive college students, being invited out to dinner and out to clubs and the more I allowed myself that interaction the hornier I found myself getting with little or no luck.

On the outside I was a decent looking guy - somewhat average at 6'3, 220 lbs with brown hair, blue eyes and a linebacker/fullback style body. I didn't have a whole lot of hair on my body and I was average in the cock department (6 ') ... I had managed to stay fit and actually worked off a few pounds during college. I guess you could say I was the typical beef and corn-fed guy from the Midwest who, now, was thrust into the land of very attractive people in a fairly glamorous coastal state. In spite of my looks and body style I was, on the inside, very shy and not self assured at all. I could speak to the state assembly or state senate or a crowd of 5000 students but a conversation with 1 very attractive individual, on a 1-on-1 basis, was really tough for me.

As my yearnings and desires escalated so did my actions. Ultimately, I found myself interacting, with the encouragement of one of my college-age acquaintances, in a gay chat room. I was actually somewhat naïve and, by today's standards, reckless as I filled out a profile and posted a picture of myself. It sure didn't take long to replace that photo with a head-less shot after some of the crazy responses I got - not to mention the fact that I was working with some pretty high-profile folks and didn't think about that initially!

After a few days I began chatting with this guy pretty regularly. As it turned out we were both named Matt and as I worked my way from the southern portion of the state, via Amtrak, on the tour of college campuses we began to start talking about the possibility of meeting when I concluded my trip in his city. The excitement of this possibility was not only concerning to me, considering my hetero roots, but also very exciting - a phenomenon I could not explain at the time.

I was at a point where I couldn't even really focus on the job and tasks at hand and I was becoming consumed with the thoughts of what this meeting would be like. Instead of going out to dinners and the local bars, I found myself shopping for new clothes (and underwear) and chatting with him well into the evenings. The train rides, from city to city, almost became unbearable because of the anticipation of the end of the trip - now only 2 days away and I couldn't get rid of the hard-on that seemed like it was going to be permanent.

'Matt' was in his late 20's and was a graduate student at the university I spoke about earlier. He was also involved in the political world in his very progressive city. He was very masculine and downright handsome (If I was to believe it really was him in the photo he shared). He was 6'5 and weighed 230lbs....had sandy blonde hair and the most amazing blue eyes. I would just stare at the photos on my computer and wonder how on earth a guy like me could 'land' someone like him and, considering my roots, why, why, why am I even considering this? Surely I could go out and land a chick and get my rocks off but, for some unexplained reason, I couldn't NOT go through with this crazy plan.

The day was here....after quick trips to two campuses I was on the train headed for the city where we would meet. I went into the restroom/shower room on the train to change from my 'business' attire to, what I hoped would be, my hot attire! I had chosen a light blue polo shirt (I was told it set off my own blue eyes) and a new pair of faded Silvertab jeans. Silvertabs were the most comfortable for me as they were tight in the ass but gave me plenty of room for my above-average size thighs.....and.....they were a little baggy in the front (Which would conveniently hide that permanent hard-on I already had). To complete it all, I chose a semi-snug pair of black CK Boxer Briefs that I thought looked pretty damn good on me. I had managed to develop a decent tan and was feeling pretty good about the outward appearance at least.

It seemed like every five minutes the intercom would announce when we would be arriving. The trip into the city was great as the train wound around the coast, inland into the wine country, and back towards the bay. With about 30 minutes before arrival I decided to go to the club car and get a quick cocktail just to ease the nerves. I swear the steward, or bartender, was giving me the serious once-over and some intense looks. I was starting to feel a little better - if not more aware!

Train pulls up......I had to work hard not to jump to the front of the line one minute...and the next I had thoughts of going and hiding in the shower room. Finally I got off. Matt had insisted on meeting me at the train station and taking me to his place. I was perfectly content with the idea of me getting a room somewhere close to the wharf - safer in my head and less reckless I thought but, he would have none of that. He wanted to make this a 'date nite'....showing me a bit of the local scenery and then cooking dinner. He assured me he was an excellent cook, had some great steaks and wonderful wine, and that we would have a very relaxing evening with no pressure. If at some point I wanted to leave or go out on the town, he assured me it would not hurt his feelings.

I stepped off the train and almost passed out. I knew immediately who he was and the photos did not do him justice! Blonde hair, blue eyes, tan, muscles and pecs in a semi-tight crew neck pullover. He was tall...and I mean the 'you totally have to look up at him' tall. He had about two days worth of scruff but neatly trimmed and it set off his strong jaw line and kick-ass dimples (I'm a sucker for the dimples).

I do not know for certain, as it's a bit of a haze, but I am sure I was not able to complete an intelligent sentence the first several minutes we were standing there. At one point he sort of grabbed my arm to steer me out of the station and towards his car - and he did so with a calming, gentle strength that almost made me weak in the knees. Shit...the whole package made me weak in the knees.

We dispensed with the normal touristy type stuff when he asked me what I thought I'd like to do....get my own room or go with him to his place.....my initial thought was to tell him I'd jump his bones at either place.....but all of a sudden I was concerned about sounding reckless - go figure. I was feeling totally at ease and, while my ego and self confidence were still a bit below where I wanted them to be, I was perfectly content going along with his plan. I was hungry, thirsty and, for the sake on not sounding too anxious, getting harder and hornier by the minute.

The 30 minute ride from the Wharf to his place was fairly comfortable. It gave me an opportunity to relax, calm down and try to get the persistent bulge in my pants to mellow out....thank god for those baggy silvertabs! Throughout the entire ride he kept looking over at me and smiling....setting off those dimples again. He kept the conversation light and non-threatening and it helped relax me...it was as if he knew exactly how I was feeling.

When we arrived at his place I was pleasantly surprised....a nice 2-story condo in a small gated complex....the building was a stand-alone (so no neighbors on the other side of the walls)...good size living area, nice backyard with a great patio and a hot tub. As soon as I was inside I became aware of the furnishings....clearly bachelor...masculine bachelor (which worked for me)....leather couch and chair....basic furniture....framed sports pictures on the walls etc......so I was really comfortable now.

Matt handed me a beer and said that dinner would be ready in a few minutes. He fired up the bbq and threw a couple of steaks on. He tossed a salad, pulled some au gratin potatoes out of the oven and it was on.....fast forwarding again...dinner was great....the conversation was awesome...he poured a couple a nice glasses of red wine and we were done.

Once the dishes and clean up was done he asked what I'd like to do.....of course my head was spinning and I immediately felt that stirring in my groin.....I asked him what he meant and he said 'I wasn't sure if you wanted to go out to the clubs...hang out here....site see' etc....I then asked the age-old deflection question...'I dunno, what do you wanna do?' He chuckled a bit.....thought for a minute and said...'Well, in my perfect world we'd throw on a pair of shorts and jump in the hot-tub with our drinks...and relax...but I'm not sure if you are cool with that'.....Cool with that, how could he be asking if I was cool with seeing him almost naked, hanging out and getting our drink on????? And of course, my reckless response, which just came flying out of my mouth was to say 'well matt, in my perfect world we'd take our drinks to the hot tub with no shorts on and try to relax'...yep, there it was like the big ole elephant in the room....I couldn't take it back now-just when I thought I had totally blown this deal he said 'I'll be right back' and he ran upstairs. I was just sure he was calling somebody to give me a ride back to the train station - how could I have been so stupid and just let that come flying out of my mouth like that?

What I saw when he came back down the stairs was my own personal version of Adonis.....this handsome, blonde haired blue eyed stud had re-appeared with two towels and nothing else.....I mean nothing else...naked as a jay-bird. I am sure my jaw dropped and I was on the verge of dropping my drink....that old weak-in-the-knee thing was happening again and that twinge 'down there' was totally obvious....even the silvertabs couldn't save me now. He must have realized the look on my face cuz before I could say anything he said 'I just thought I would bring it to the level we both want and not go around it'.......with that he handed me a towel and said I could change upstairs - he was going to turn on the hot tub and the jets.....well....needless to say...he had already turned my jets on! So I headed upstairs with my bag.

I accepted the invitation, took my clothes off, wrapped the towel around my waist and headed downstairs to the back yard. When I went through the door he had his back to me leaning over the edge of the hot tub working the controls....that view was the hottest I had ever seen - no tan lines.....tight cuppable cheeks with a little dusting of that blonde hair....oh my god. Instantly there was no reason for me to be modest and I certainly couldn't hide it as my dick jumped to attention. He turned and, thinking the back was the best view, I was totally wrong - this guy was a god.....great body as I said before and the most perfect cock I had seen - it was about 6', pretty thick and cut....but when I looked at the whole 'package' I thought the guy ought to be in pictures or show biz at the very least!

Matt climbed over the edge putting one foot in the water first and when he did I got another intense view from the back....him straddling the edge of the tub with his cheeks spread a bit and the ball sack dangling a bit...holy shit...was this real?? He got in and turned around and the water came up to just about his navel. That brawny stomach and chest was making my head spin and, for a moment, I found myself second guessing this whole thing and the decision I had made - 'What the fuck was I doing - I'm into women and yet this guy is just damn hot and it's got my juices going'.

As I was scanning the backyard for exits and playing in my head the excuses I would use to get out of there I came back to reality when Matt said 'Come here for a sec' - I kind of was puzzled and he said it again in a soft and coaxing voice ....I moved closer to the tub and he raised his hand up along the side of my face - gently stroking it and running a finger down my neck to the middle of my chest and then it happened.....He leaned in and kissed me as he held the back of my neck. For the moment it was the most passionate thing I had ever experienced - it was like time stopped. When we separated he looked into my eyes and told me that he'd wanted to do that from the minute he saw me through the train window.

Part 2

Well, needless to say, that moment of passion along with his gentle verbalizing of his desire to be with me sealed the deal - I was no longer looking for exits or excuses and I dropped the towel and climbed in - even though my head was telling me that if I do this there would be no turning back I climbed in with no hesitation. It was almost one of those slow-motion moments and felt somewhat surreal as I climbed over the edge....literally AND figuratively. As I entered the water I was aware that the jets were on, there were some bubbles, the water is comfortably warm but not too hot and then I really was consumed with the moment. Matt moved to me and embraced me like has never happened to me before and again, we kissed for, what seemed like, an eternity. The kiss was sensual because as it was happening he was running his hands slowly and gently up and down my back from the top of my ass to my shoulders. He then cupped my face in his two hands and looked into my eyes without ever saying a word...well....his eyes spoke many words.

Matt sat down on one of the seats in the tub and pulled me close to him and, as I sat in front of him, I was keenly aware of two things....his cock was very hard and was resting upward along my back and my cock was rock hard as the swirling water from the jets and the intensity of the moment rocked my world.

We sat in the position for almost an hour with very little movement other than his soft caresses of my chest, pecs and stomach all the while nibbling and kissing on my neck and ears. When we spoke it was soft in tone and mostly about how enjoyable, relaxing and soothing it was. At one point Matt moved and got out to refresh our glasses of wine and when he came back he resumed the same position - it was almost like he felt it was important that this time be non-threatening and comfortable for me and it was - My inhibitions and concerns about recklessness were quickly going away thanks to him and I reveled in the realization that we were sitting there watching one of the most glorious sunsets I have ever seen (or, for that matter, paid attention to) and I was in a place that felt safe and very natural.

It wasn't long after the sun went down that Matt stood up and reached for my hand. He suggested that we get out before we 'shriveled up' (Of course, in my head there was no chance of anything shriveling!). He got out first, grabbed a towel and then I got out and he proceeded to dry me off - head to toe. 'What would you like to do now? Hang out here, get dressed and go check out a few clubs? Maybe grab some coffee and dessert?' I responded by telling him that I was perfectly content with any of those suggestions....he then said 'Well, in your perfect world' and I interrupted by telling him I was perfectly content just hanging out. His response was 'perfect-I didn't really want to get dressed just to go get dessert!'

From that point, with towels wrapped around our waists, we lounged on the couch and nibbled cheesecake and each other while watching a short, independent film. It, again, was one of the most comfortable and natural experiences of my life. I knew then that, whether this particular encounter would materialize into something more or not, that my fate and desires and preferences were made very clear to me.

Part 3

With dessert plates washed and put away , we two Matt's, headed upstairs and when I got in the bedroom I realized, at some point, he had snuck upstairs and lit candles and put on some very soft music. Dimly lit, the room had an air of extravagance and left me with a sense that something very special could happen.

With that gentle but strong way he has, Matt led me to the bed, undid my towel and suggested I lay down on my stomach. Not really sure what he had in store for me I was a tad bit anxious but that feeling quickly went away when I felt his strong hands rubbing massage oil into my neck and shoulders. For the next 30 minutes or so I basked in the most incredible massage I have ever, even to this day, had.

When he urged me to turn over I realized something and I said 'Matt, this whole afternoon and evening has been incredible. You have gone out of your way to make it that way but I don't think it's been fair to you'

'Why would you think that?' I said 'because it really hasn't been a two way street here - dinner, the hot tub, dessert & wine, the massage - I am not sure what you are getting from all of this'

and with that he put his index finger to my lips and said 'shhhh' 'but Matt' 'shhhhh' and he kissed me again, that fire and passion there again, and I was lost in it.

Over the course of the next several hours I experienced feelings and sensations that I never knew were there. As we lied on the bed Matt ran his tongue from my neck the entire length of my chest and down to my toes - I can't even begin to tell you how erotic that was. He circled the tip of my cock with his tongue for, what seemed like, days. At several points, I had to guide him away as I was just sure I was going to shoot and I wanted to 'last'.

We sat up and I really wanted to experience the touch and feel of his body and that kick-ass dick and I told him so - he responded by saying 'Matt, you can do or touch or taste whatever you want to...I am all yours' so, not being one to look a gift-horse in the mouth, I embarked on a journey of touch and feel and taste. I had not had a cock in my mouth since the summer with my cousin and, though it was more than once that summer, I did not recall enjoying that like I was enjoying this.

Matt's cock was perfect, at least in my novice mind. It was a little more than 6 inches and relatively thick. It had a nice head and he was cut...the whole thing just looked absolutely right and perfect for his body. It took me more than one try to get it all in my mouth and he was gentle and patient as he led me through the process of taking it all in. He guided me to pay attention to his balls and I licked and sucked them, taking each one into my mouth at various times. He would move his body in certain directions which focused my attention on the parts he wanted me to focus on. Somewhere in the mix of it all he took the lead and gently pushed me down on my back - again he went at my cock with his mouth and tongue but then....another feeling I had never had....he went beyond my balls to the nether-land.....and the next sensation was his tongue circling my asshole. He gently lifted my legs a bit to allow him better access and I swear he spent the next 30 minutes alternating between my hole, my nuts and my dick. At least once while his hands were massaging my chest and he tweaked my nips a bit and I thought I was going to explode then and there.

He continued the cock and ball and hole work for a few minutes and then he slowly slid himself up towards my head - his tongue never losing contact with my body and, for a minute he paid particular attention to my nipples causing me to squirm on the bed. We were face to face again and I was looking into those eyes while our cocks assaulted each other. We were both wet with pre-cum and the contact was amazing. As he was kissing my neck he said, in his passionate voice 'Matt, I want to make love to you!!' All I could say was 'Isn't that what you've been doing' and, as he looked up into my eyes, I saw that smile and those dimples....damn those dimples!

Another word did not have to be said. Maybe it was the expression on my face or the look in my eyes, or maybe it was the fact that my dick was bouncing around like it was chasing something. Considering all those things, Matt then embarked on a trip that I would never forget. He inched his way slowly, and I mean painfully slow, with his tongue back down the entire length of my torso, circling my nipples for days, down my stomach and then around and over my cock. His hands rubbing my thighs as he nestled in, again, with his head between my legs. Methodically yet erotically he worked my cock and balls and hole alternating the use of his big hands and his expert tongue.

At one point, as I struggled to contain myself and touch him at the same time, I reached for his cock and realized he had slipped a condom on - this guy was amazingly smooth cuz I never heard the wrapper, I never saw him put it on and I certainly had no idea what happened next was coming.

It is almost impossible, for the sake of the story, to recall all of the intricate details of this man's skill or the things I was feeling. It is also almost impossible to adequately describe what was going on in my head because I don't know - all I knew at the time, and know now, is that this was turning into the most incredible experience of my life - I didn't know where it was going, but I sure didn't want it to end.

After I got the feel of the condom Matt realized and then he slowly and gently placed his hands on the backs of my legs and started to raise them....Instinctively I scooted down towards the end of the bed a bit and he just smiled....yep...those dimples again. I think he realized I realized and it was a go.

He grabbed a hold of the base of his dick and the outside of the condom was lubed - he rubbed his dick all around mine, my balls and then began slowly circling my hole each time placing the head at the opening. I was not at all sure what to expect at this point but I sure as hell was going to go with the flow, so to speak.

As he lifted my legs a little more he massaged my thighs and gently played with my cock. Every time he touched it another large gob of pre-cum flowed out and, at one point, he took a bit on his finger and put it in his mouth and the kissed me again. As we were kissing I felt the pressure of his dick head moving past the outer ring of my hole and as he moved it in further his kiss and touch became more and more passionate. It was then, as he was fully inside me, I think he hit the mother lode. He could tell by my reaction that he had hit the prostate and the green flag was waving. He moved his hips and slowly slid himself almost all the way out and then back in, each time hitting the nugget. As his pace increased so did the temperature in my ball sack - I truly believed I was at the boiling point and I told him so. He pulled almost all the way out and then his hands went to work on my chest as he leaned up to kiss me. Each time he would move towards my face his cock would go in a little further and then he would move down to my chest with his lips and his cock would move almost out again. I'm not sure if it was intentional to slow things down or if it was just happening because of the similarity in our body size and height but, for whatever reason, it was keeping me on an even keel as I realized he was not quite ready.

As he made his way back up and attempted to kiss me I smiled - he looked at me with his headed cocked to the side and said 'what' - I just looked at him and said 'let's do this' and do it we did. He took me to the brink immediately as he focused more on the act rather than my body. It was almost as if he was waiting for permission and, while what he did to my ass couldn't be considered an assault let me tell you it was intense. He decided it was time and his thrusts and pumping were almost relentless. I could literally, I think, feel the blood pumping in his dick and I loved the determination on his face. He never took his eyes off me as his balls slapped my ass and his hands never left my thighs or my balls or my dick.

The cum-gods were calling and I told him that it would only be mili-seconds and I was gonna blow - he pulled almost all the way out, smiled and then picked up the pace...each freaking time he hit the nugget harder and harder and, with an uncanny sense of me, he grabbed my dick, leaned over and stuffed it in his mouth. It was incredible because he had his dick in my ass to the hilt and, I guess because of his height, he was able to lean over and get my cock in his mouth. His thrusts were totally in sync with his mouth on my dick and.....then I blew.....I didn't even have a chance to do anything to let him know other than grunt and let out, what I am sure was, a blood curdling scream/moan...or something like that...I pumped and pumped and pumped what I know to be the largest I've ever blown and he swallowed and swallowed - only losing a bit down his chin. As I was coming down a bit I realized, by the look on his face and the bulging vein in his neck that it was gonna happen now and, with that, he straightened up, grabbed the back of my legs and jammed in twice more and then let out a huge groan or scream of his own. The nerve endings in my ass were on fire as he pumped several more times before slowing down a bit but he continued to push back in to the fullest and pulling almost all the way out. This went on for a few more minutes and then I felt him begin to soften. I am sure my ass was totally numb as I didn't even feel him pull out.

Catching his breath a bit and dispensing with the rubber he climbed up between my legs again and worked his tongue all the way, and I mean all the way, up to my neck. He rested on top of me with his legs on either side and we kissed for, what again, seemed like an eternity.

It was at that point that I realized that you could see faint traces of the sun coming up through the window blinds and, whether it was from the 22 hour day or the intensity of our lovemaking, I was exhausted and spent. I would like to think, and tell you that I came 10 times that night but I can't. What I will tell you is that, at some point about daybreak, we fell asleep in each other's arms. When I woke up a few hours later I was content to just lay there and listen to him breathe as he slept, spooned behind me with his arm draped over me. It was then that I realized, maybe with a little of that reckless abandon, that this would be my life.

Epilogue

I would sincerely like to tell you that, from that day on, the two Matt's have been together but, I can't. Our relationship was able to stand the test of time and even the 120 miles that separated our two towns. What it wasn't able to do was stand the test of our careers and where each of us wanted our lives to be so we, after 4 years, went our separate directions. He to become a very successful and well respected college professor and I, well, the activism catapulted me into a career in politics...well not public office, but helping others get there. My traveling days have never ended and it became harder and harder to be together - mostly my responsibility and, in most respects, I truly regret that.

I will tell you that, 10 years after the split we are best friends and will always be soul mates. I will honor and love that man for the rest of my life because of who he was and who he has become and, most importantly, because he showed me who I was and am.