New Territory

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A young man's first experience with his fellow gender.
1.9k words
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The evening had begun like many others spent with Jay's father, Jeremy and his father's partner, Davis. There had been many pleasant weekends spent together building the friendships since we'd first been introduced earlier that summer, sharing exceptionally good food, good company, very good herbs, amusing board games, pleasant wines and on a couple occasions my introduction to their group's regular gatherings for the somewhat venerated cocktail party.

I had been introduced to Jay's father and his long time lover over an earlier weekend spent together with my high school friend during my nineteenth summer. We'd decided on a whim to arrange a briefly arranged visit with his dad, one I strongly encouraged upon finding out about how they'd been estranged for so long, and his expressed interest in renewing a friendship with his father. The friendship emerged quickly as I was surely young and certainly inexperienced, having only taken two lovers by this point in my youth. I had little recognition at the time that I was being gently groomed.

There had been so many discussions after considerable libation about the facts of taking a same sex lover and the day to day pros and cons of maintaining such a relationship. I learned quickly that to take a male lover would have incredible advantages, even beyond the intimacy with someone with a far better understanding of how the male body responds. I was skating along the thin ice of my gender identification long before I realized there may be any sort of peril. I had so much curiosity about the life, and what it entailed, and so few reservations about exploring my curiosity with questions due to my personality at the time, I didn't realize I had opened Pandora's Box, so to speak.

I had been so damn horny all that day and their discussion had been exceptionally candid that evening that I was finally enticed by my thoughts and my hormones to slip into their room at about one in the morning as they slept, only to awaken and surprise them both with my question, asking them to be gentle and asking If I may join them. I somewhat bumbled my request due to my nerves, but quickly clarified my request, hoping they would understand my exceptional nervousness.

Jeremy and Davis asked me to excuse them for a minute so they could discuss my proposition and after a very unnerving moment in the hall where I felt my surprising emboldened courage wavering, I was asked back into the room to join them. I was amazingly nervous and so very self conscious. Jeremy was in his early forties, 5' 7", somewhat broad shouldered, his black hair and goatee were starting to turn salt & pepper with the beginnings of grey, he was deep voiced although often soft spoken with sharp eyes that were slate blue/grey. Davis was just a little older; around 6' tall, with sandy blonde hair that was lightly fading at the temples, a larger natural build with striking hazel/green eyes. He was somewhat louder in his tenor voice but was eloquent and disarmingly intelligent.

We three soon discovered shared many interests and had quickly become friends in spite of Jay's ongoing strained relationship to his father. Many weekends had been spent together with Jay's abrasive attitude causing unnecessary tension amongst everyone, his rebellious nature and more youthful mindset seeking a path of its own, that eventually I had begun to simplify things and spend time with my new friends on my own. This led to my more open feelings about exploring this side of my personality; the decadent, visceral and bacchanalian young man who lives primarily for the experience of life itself.

And so, I had asked to join them, their room dark and unnerving, they had discussed it amongst themselves and had decided to let me join them. When I came back in, I was immediately kissed by Jeremy, dull, on the lips and hi tongue began to quickly tease between my lips and I began to caress my tongue, entwining it with his. Meanwhile, Davis was gently and warmly hugging and caressing me while Jeremy and I were exploring each other's tongues and lips. Then I felt Davis gently lifting my t-shirt over my head, and as my collar and shirt interrupted my kiss with Jeremy, I turned and kissed Davis deeply while my arms were trapped over my head in my shirt.

During our first kiss, I felt Jeremy caressing my torso and his hot mouth immediately locking onto my nipple. My cock had been hardening on and off all evening as I contemplated this meeting and now with a very good kiss and my nipple being suckled while the rest of my body was being cupped, caressed and sensually massaged, I became harder than I ever recall having been , much to Jeremy's hand's delight, he quickly unbuckled my jeans and freed my leaking erection, caressing my slick precum all over my downward curved shaft and then taking me quickly and deeply into his hot mouth to almost immediately attempt to deep-throat my throbbing cock. He quickly mentioned to Davis about how my bend fit perfectly down his throat and I was immediately guided to the bed where they both lay me down and began to trade off between licking and caressing my balls, and taking me in their mouths as deeply and deftly as possible, I almost came immediately. Davis caught this and they both paused while Davis was gently squeezing the base of my cock to calm me down and prevent me from shooting my cum all over everything just as we were getting started.

They took that moment to shed the rest of their pajamas while constantly maintaining contact with me, fondling or caressing the nearest erogenous zone on my body as they disrobed. They both returned to switching back and forth between by balls and my cock, sending me into an almost frenzied state of arousal. I asked them both to turn their torsos toward my head so I could try to return the favor. I was fondling and caressing them as much as I could while they'd been sucking me. And now with a cock on either side of my head, I chose to fully commit to the situation and took Davis' long cock into my hand and mouth to begin sucking him like how I imagined I would like it, all while stroking Jeremy's thick leaking cock in my hand as sensually as I could imagine would feel wonderful to me.

Davis was groaning as he sucked and licked on me and suddenly exclaims, "Oh my god, you're a natural! You've really never done that before?"

I giggled and told the truth, "No, never. I'm imagining what would feel good to me the way you both had described." Then turning my head, I took Jeremy's thick cock into my mouth and slowly went all the way down to lick his balls while he slid into the top of my throat. Jeremy yelped out, "Oh god! I'm gonna cum!" after only a few minutes of my apparently talented deep throat work on his fat cock and so I switched to heavily licking his big mushroomed cock head while stroking his fat shaft. He groaned very loudly and his warm, thick cum shot out over the top of my tongue, giving me my first taste of a man's seed, and landed all over my shoulder and neck.

I was splattered but I had enjoyed the wanton and sultry sensation. Then, suddenly, Davis was there, licking and sucking on my neck and shoulder, cleaning his lover's dripping cum off of my young body. I had been so distracted with my giving head that I had not really approached an orgasm, and now Jeremy in his full rut and was completely focused upon my cock, sucking me deep with long strokes along his firm, textured tongue. Good god, ...it was so stimulating that it was too much, but because I was so inexperienced and so eager to please that be pleased that I didn't realize I was being over stimulated. His hands were under me, caressing and squeezing my ass, fingers fondling my puckering asshole. Wow! That was a first! And it felt amazing!

I began to suck on Davis again as Jeremy teased my cock and my ass and then Davis asked, "Do you want to try anything else?" - The very question I had been ruminating over the entire time I had been in their bedroom.

Eventually I said, "Yes, I do. -- But I don't know what to do"

That was when I learned just how wonderful and exceptional my new lovers were. I could not have been luckier -- or more self conscious to learn that I truly *was* a natural.

Jeremy asked if I wanted to try one of them inside me. I said I did and he said I should try with Davis first because her was worried that he was too thick for me to start with. I was grateful for his suggestion shortly thereafter because after he lubed and fingered my asshole while Davis sucked me some more we had Davis lay down and I began to slowly slide my asshole down over his big long rigid cock while I faced away from him. It was as astonishing feeling, being so full and then Jeremy taking my cock in his mouth. I was so damn turned on, that I soon began to ride Davis' hard member and fuck Jeremy's mouth with abandon. Davis said, "I can't believe you've never done this before, that's my favorite position for my partner because it's the deepest I can go. I love how your fucking me so slow and deep!"

Then after a moment's discussion I said I wanted to try Jeremy's thicker cock. They were both quite cautioning about it, but I eventually was laying on my back with my knees up to my chest as Jeremy's hard fat cock penetrated my freshly de-flowered, and well lubed ass. Dear God his cock was thick! I was grateful it wasn't any more than six and a half inches -- I would have ripped in two. As it was he was sliding into me very slow but plenty deep as Davis was sucking and stroking my cock and my balls while I took him into my mouth again to keep him hard and stimulated.

After a little while of slow thrusting I needed a break from Jeremy's monster thickness. I felt like I had been riding a tree stump, but I didn't want to fall off the horse, so to speak, so I had Davis enter me from behind and slow fucked him with my ass until he had a huge orgasm, throbbing warm jets of his cum into my ass while Jeremy stroked me. Once Davis came, I wanted to cum too, so I had Jeremy lay down and rode his rigid pole while Davis sucked me and fondled my balls, gently tugging on my sack.

The massive orgasm that had been building in me this whole time finally came to the crest and with Jeremy's cock doing amazing things to my prostate and Davis' licking, sucking, stroking, caressing and tugging... they finally coaxed out of me the most massive orgasm my young body and mind had ever experienced. Davis was licking the underside of the head of my rock hard cock with his very textured tongue as I dove over the edge orgasm and spurting what felt like gallons of sticky, salty, yummy cum all over his cheek and my chest...

And then I woke up. Their smiling faces and their cuddling, fondling questions of, "What would you like for breakfast?"

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AnonymousAnonymousalmost 5 years ago

This story had my cock hard in nit time as I read it it was very descriptive of what was happening & made me imagine I was the lucky guy being seduced by the 2 more experienced guys fucking both & being fucked as being in a 3some is a fantasy of mine that I have yet to fulfil

AnonymousAnonymousover 6 years ago
Good writing

You need to continue writing gay stories. You're very good at it.

AnonymousAnonymousalmost 7 years ago
Threesome

I had my first when I was 19 the two other guys were 52 and 56 respectively .. John ( 52 ) was my Daddy who had persuaded me to meet with his friend Ray ( 56 ) at his beach house that weekend ... John had bought me a new lingerie outfit for the occasion which I had to wear to impress Ray .. And 'boy did he like it' , I was covered in cum in no time ...Johns , Ray's and my own !!

I must have sucked them both off at least 5 times each that weekend as well as them both fucking me !!

AnonymousAnonymousabout 7 years ago
that was my first fantasy

my first fantasy would be to have two older and more experienced guys lay me down between them while they likcked and slurped on my body for an hour. Every place a tongue felt good , I got tongued there! After cumin and washing up. The question was posed to me. "Do u want to return the favor?" "NO!" was my initial thought. then when I figured out that I could tell my self that I had no choice, it was easy for me to lean in and take that first cock in between my lips.I almost came when the first cock twitched when my mouth clamped onto that hard purple head. He warned me that he was going to cum. I was so hot and wanting to make them feel good, they both ended up cuming in my eager mouth! I swallowed their cum and they applauded me. I was wearing lingerie by the end of the day. I was rock hard.

MaricopamanMaricopamanabout 7 years ago
Details

The story got my cock hard. I would have liked to have known more about each man,hairy,smooth, cut, uncut. I liked.the description of feelings and sensations.

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