The Path Not Taken Pt. 01

Note: The following begins as a true story of how I lost my virginity (anal and otherwise) to two gay top daddies when I was 19. Now, 10 years later, I look back on this experience and fantasize about what could have been if I had just embraced my inner cock slut...and the result is this story series. The first installment will cover the true events and transition to the lost fantasy. The story teller in me necessitates a lengthy back story so skip down to the 4th or 5th paragraph to get to the fun.

It was the summer following my freshman year in college. I had lived on campus for the regular term, despite my childhood home being only 20 minutes away, and fully embraced the freedom of college life. I joined a fraternity and partied heavily whenever I could and my grades had taken a hit. I now found myself making up some courses in the summer semester and waiting tables to pay for my habit of cheap beer and dank weed. My scholarship did not cover room and board for the summer term, so I moved back into the basement apartment at my parent's house. Between classes and work and the fact I had my own door to the driveway, they never really kept tabs on me and I enjoyed all the freedoms that a college kid should.

College life was great for me so far, but for one major problem: I was terrible with women. I always ended up in the friend zone and so, in spite of my best efforts, I was still a virgin. I wasn't a bad looking guy either at 5'9 180lbs and muscular but with what would now be called a bit of a "dad bod." I was decently equipped with a thick, 6.5in cock that was being wasted on my right hand. The alcohol, chronic virginity, and the weed combined to create an insatiable horniness and an above average porn habit.

Like so many "curious guys," my trip down the rabbit hole began with shemale porn. For me, it was truly accidental, but after enough of it I began to see that cocks can be truly beautiful. Then I stumbled on TS Seduction. I watched as sexy women with beautiful big cocks seduced normal straight men (like myself) to suck cock and take it up the ass. Never had I been so hard. Seeing how much they enjoyed taking cock up the ass made me so curious. It started with a finger, then 2, then hairbrush handles and moving up to a small dildo I ordered off Amazon. -I loved the feeling of having my ass penetrated. That lead to gay porn and the porn lead to cruising craigslist.

I started out just cruising the personals, reading posts and jacking off to the pictures. One day I got brave. I had smoked a big fat bowl, got super horny edging to some porn, and decided to create a burner e-mail and post my own ad. It read something along the line of: "curious 19yo looking for first time experience. Would like to try giving/receiving oral and possibly bottom. Must be clean and DDF. Safe play only." I snapped a pic of my hard cock and my ass bent over and attached those and hit POST. Not surprisingly, I got a ton of responses and mostly from older men. That was something I had not considered, but found very hot. I would go on to attempt meet ups on 2 occasions but chickened out, getting as close as actually knocking on the 2nd guy's hotel room door, meeting him, and then telling him I couldn't do it.

You know what they say though: third time is a charm. Weeks passed and I stumbled across an ad with the subject: "Two Bama Tops." I clicked to see more and was met with a pic of two glorious, thick, cut, 7+ in cocks. The body read that they were in their 40's, DDF, experienced tops looking for younger guys to hangout in their hot tub and fool around in the hot tub and the "swing". If I wasn't already hooked, I was when I clicked on the second picture: a sex swing. I responded, we traded pics, stats etc., and then I flaked. In a moment of lucidity I opted to try and hold on to my masculinity and straight dignity.

2 or 3 days later, I found myself over at some of my frat bro's house smoking some weed after work and classes and decided to message the 2 bama tops to see if they were free. I was so horny and the weed made me where I could care less how I got laid. They replied and told me they were heating up the hot tub and to be there in an hour, address enclosed. Their house was only 15 min away. I got nervous, but I knew this was what I wanted to do, plus they were so nice and low pressure. I figured I would go over there, chill in the hot tub and just see what happened. Still, just in case, I decided I should be ready to get my cherry popped. I took a cheapo bottled water with me into the bathroom and used it to make my ass clean and ready.

30 minutes later, I was pulling up in their driveway. I walked up to the door and knocked. A handsomely average guy answered the door in his gym shorts and told me to come in, they were glad I made it. As I entered, I sized him up. He was geeky with glasses and a dad bod, but I felt immediately at ease. He introduced himself as Steve and introduced his partner Jay who was sitting watching TV, seemingly disinterested. Steve told me the hot tub was ready and told me to take my clothes off and follow him. I did just that and stripped naked right there in the foyer and followed Steve towards the French doors across the room. He stripped his shirt as I followed. Nervous about being naked in front of other guys, I hurried into the hot tub and watched as Steve pulled down his gym shorts to reveal his semi-erect cock. I got situated in the middle of the far side of the hot tub. Steve took a seat in the corner to my left. Somewhat to my surprise, Jay appeared at the steps to the hot tub, already nude, sporting the biggest, thickest softie I had ever seen. I wanted it in my mouth so bad. He got comfortable in the corner to my right.

So here I am, a 19yo "straight" virgin, naked in a hot tub sandwiched between 2 40+ yr old naked gay tops. There was some small talk, mostly about what I had/hadn't done and what I absolutely didn't want to do. I told them I was a virgin but had played with toys and that I was open to trying just about anything but rimming and kissing. I had my eyes closed and was leaned back relaxed when I felt 2 pairs of hands begin to lightly touch me. They touched me on the thighs and the chest first, and then found their way to grazing my ass and my cock. I was already rock hard. I may have been struggling with these events in my mind, but my cock gave me away. I wanted this. I loved this.

I reached my own arms out and my hands were greeted with erect cocks on both sides. With the jets on the hot tub, I couldn't really see what I was touching, but from what I could feel, Jay was the bigger of the 2. He was almost 8 inches and too thick for me to wrap my fingers all the way around. Steve was slightly smaller at 7.5 and not quite as thick but he had a fat mushroom head that felt so good popping in and out of my hand. Jay was stroking my cock now and Steve moved between my open legs. He scooped his hands under my ass and lifted up. Instinctively I raised my hips so that I was floating with my cock and balls above water. He took my cock in his mouth while fondling my balls and Jay took advantage of the accessibility of my ass and began rubbing my asshole. I was on cloud 9 and horny like a bitch in heat. After a few minutes, I sat up and looked toward Steve, who took the hint and laid back to give me access to his cock. Jay moved around next to him. I took Steve in my hand and for the first time got a good look at what would be my first cock. I began sucking on his big mushroom head and it felt so at home in my mouth. I didn't really know what I was doing, but I tried to mimic what I had seen on the internet. I lightly sucked on his head while flicking the underside with the tip of my tongue and then tried working more and more of his length into my mouth and throat. I was clumsy but enthusiastic, and he coached me on how to not use teeth and to open my throat by sticking out my tongue, etc.

Out of the corner of my eye I saw Jay stroking his own glorious cock and decided it was time to have a taste of him. While I went to work, Steve found his way behind me to continue getting my hole ready. He was so gentle and sweet. First he just rubbed it like Jay had done, then he asked if he could rim me, I welcomed his tongue and it tickled so good. He tongued my ass while I continued to get used to sucking his partner's fat cock. After a while he slipped a finger in me and I moaned. He asked if it was ok and I assured him it felt so good. My pussy was not stranger to the sensation of a finger, but having a stranger invade me felt so much better. He worked a second finger in and then stopped and asked if we were ready to go downstairs. I didn't know was what was downstairs, but whatever it was I knew I wanted it. I wanted to feel these cocks in my virgin ass. We got out of the hot tub and toweled off before I followed them into the house and downstairs.

It was immediately obvious that the basement had a very specific purpose: fucking. Against the wall to the left at the foot of the stairs was a glass fishbowl full of condoms and a big pump bottle of lube. Just past that towards the middle of the room was the sex swing and then there was a seating area around a large projector screen. The seating area featured two couches opposite each other and then opposite the screen was a long upholstered "bench seat' which I assumed could allow for some interesting sex positions. Steve motioned for me to lay back in the swing while he went to the fishbowl and began putting on a condom. My nerves hit me again, but I was too intoxicated with lust to stop what was already put in motion. I hopped back into the swing and put my feet up in the stirrups. Looking between my legs, I could see Steve approaching with his cock gloved up, stroking some lube on his cock. Jay came around to my right side and put his cock in my face. I knew what he wanted and opened my mouth wide to allow him to fuck my lips. Steve grabbed my hips so that my ass was right at the edge of the swing back and gently massaged lube into my asshole, first with one and then two fingers. My attention was occupied by servicing Jay with my mouth, but I felt Steve's fingers pull out and then I felt tremendous pressure on my hole as he tried to force that mushroom head into my virgin ass. I pushed back against it and all of a sudden it popped inside me. I felt the briefest twinge of pain followed immediately by overwhelming pleasure and a feeling of fullness. My cock stood straight up and throbbed as he both pushed himself forward and pulled me and the swing towards him, impaling his cock deeper and deeper inside me. Jay took advantage of my gasp of pain and pleasure and forced his own cock balls deep into my throat. I gagged and moaned all at the same time.

Steve slowly worked himself into me until I could feel his heavy balls resting on my ass. He pulled out slowly until just the tip was left straining to exit my tight ass and then slammed back into me with one swift thrust of his hips and simultaneous pull of the swing straps. I gasped again in pleasure. My inner slut broke out at that moment and I took Jay in one hand feverishly working his cock with my hand and mouth and bucking my hips as Steve ravaged me at an increasing pace. He worked my virgin ass until he could pull out completely and slam back in balls deep totally unabated. He pulled out one final time and high fived Jay who pulled out of my hungry mouth and went over to the condom bowl to prepare for his turn. Steve unsheathed his beautiful member and brought it over to my mouth to let me pay homage to the cock that just popped my cherry. While I thanked Steve with my mouth, Jay wandered over between my legs and positioned himself to give me a second helping of daddy dick. I figured after the pounding from Steve, I wouldn't even struggle to take Jay. I figured wrong.

In the brief time it took for him to glove up, my asshole snapped back like a rubber band to near virgin tightness. He held the swing still while pushing and pushing, but I was just too tight. He returned with more lube and this time he broke though and it felt like I was being split in two. He waited for me to get used to his girth for a moment, but was much rougher than Steve had been. He wasted no time taking full, powerful strokes into me. I was catatonic in pleasure. It must have been good for him too, because he didn't last more than 10 minutes of fucking and grinding my teenage hole before, in one swift motion, he pulled out, removed the condom and erupted. He shot thick trails of cum from my belly button to my forehead. A few drops landed on my lips, still wrapped around Steve's cock, and I licked them clean tasting my first sample of another man's cum.

I assumed Steve would finish in my mouth, but he must have been inspired by the work Jay had done and did not want to be upstaged. He returned to the condom bowl and quickly ended the feeling of emptiness that was left inside me after Jay had pulled out. Steve fucked me slow, hard and purposefully while gripping, but not stroking, my hard cock. It wasn't long and I felt an orgasm building in me like nothing I had felt before. His fat tip was stroking and massaging my P-spot and I could feel the cum just building up in my cock until finally it erupted without any physical stimulation and pumped spurts of cum timed with his thrusts. I was having my first sissy-gasm and spewed cum all over my chest, neck, and face joining the load previously dropped by Jay. All of this was too much for Steve so he pulled out and jacked his cock pumping his own daddy juice directly to my face at near point-blank range. I must have looked like a real slut laying on my back with my legs wide, freshly gaped asshole exposed, and drenched in cum. The feeling of the warm reward dripping down my face was unreal. I could not help but sample a taste that ran across my lips.

Steve helped me up from the swing and Jay gave me a playful slap on the ass cheek and asked me how it was. I was in a totally different place, pretty much in a trance. My cock was still tingly with the remnant waves of my internal orgasm, my ass was both sore and missing the feeling of being full, and my head was swimming with thoughts and questions. All I could mutter out was "Yeah...that was fun." Steve led me upstairs to their master bathroom and laid out some fresh towels and brought in my clothes. He helped me get the shower started and left me there with my thoughts to clean myself up...

I left their house that day a changed man, trying to convince myself it was a onetime thing. It wouldn't be, but it was months before I found another guy on Craigslist. By the time I reached a place of comfort in the duality of my sexual desires (as a man who loves women, but lusts to be sexually dominated by men) years later, Jay and Steve had moved to another state. The following stories will explore where things could have gone after I got out of that shower. I hope you enjoy.