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GAY SEX STORIES

Love Is Where You Find It

Love Is Where You Find It

by Shelbydawn57
19 min read
4.93 (10000 views)
gay malecrossdressingromanceanaloral
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No need for caveats here. It's in Gay Male and you know what that means. Our key players are well over the age of consent, and you know I always deliver that happy ending. For those of you that ride, we've got a few trips out into the hill country. Some of you may know the bar this starts in. It's one of the many Austin landmarks I use in my stories. Enjoy the story and please leave me a comment if you feel so inclined.

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"Damn, check this out. Can you believe what these guys want to charge for a ride? I mean, it's only six miles." Doc showed me his phone.

It was a weird chain of events that got me here. I had been commiserating my shambles of a personal life with my waitress at the sports bar I usually went to, and she just called me on it, all of it.

"Well, you're sitting alone in a bar full of scantily clad girls too young for you to date. Not to mention all the testosterone fueled men that think they have a chance with the waitresses. To be honest, you're probably just as interested in the men as you are in the girls. You're in the wrong market."

"What? How?"

"Besides your nails and bra, I just see things in people. Can you tell me I'm wrong?" All I could do was shake my head no.

Luna had nailed me. I was a sixty-five-year-old closeted, bisexual, cross dresser working remote. My chances of meeting someone, anyone interested in me, were slim. Especially here.

"Look, you're a good-looking man, and a nice guy. I know a place..." she continued.

Two weeks later I was in this little sports bar downtown, just off Fourth Street with some guy I'd just met, listening to him complain about the cost of his Uber home.

I couldn't really complain. If I wanted to be with a man, he was what I'd look for. About my age, probably a little older. Tall, six-six, maybe more. Rugged good looks with a Pierce Brosnan thing going on. He even had a slight Irish accent. He'd just come in and sat down next to me, introducing himself as Doc. We had rooted for our Longhorns and drank and laughed.

Now and then, he'd touch my arm, or put his hand on my shoulder and lean in to whisper a joke in my ear. Most of them were very off color and funny as hell. When he came back from the bathroom, his hand always seemed to find my back. The last couple of times, his finger had traced the band of my bra as he slipped back into his seat.

"Six miles. Where do you live?" It didn't really matter, six miles out of my way was nothing. Besides, I was loving his attention and didn't want the night to end just yet.

"Just across Redbud Trail, off Westlake Drive."

"If I wanted to take the scenic route, that would be right on my way. You ever been on a bike?"

"You sure?" He was pretending to act like he was imposing. I could see his want to in his eyes and could feel mine in my stomach.

"Sure. I don't have a helmet for you, but it's only six miles, right?" I knew the implications of what was happening. It was why I had come down here, after all. It was a step into a world I had only dabbled in, but if it worked, it was an intimate, personal connection. That was something that had been missing in my life for a long time.

When I pulled into traffic, and he wrapped his arms around me, I knew I was right. This ride was going to be so much longer than just the twenty minutes it was going to take to travel those six miles.

"Can I talk you into a nightcap?" There was the offer. Doc slid his hand across my back, squeezing my upper arm as he got off my bike. This wasn't totally foreign territory. It had happened before, two or three blow jobs, and that one guy I'd met on Craig's list that I'd let fuck me. I knew I could do it. I just needed to say yes.

Closing my eyes and taking a deep breath, I told myself it was what I wanted. I just never let myself believe a guy like me would ever meet anyone in a sports bar filled with twenty-something kids; even if locals knew the area for being friendly to alternate lifestyles.

Hell, one of the best-known gay bars in the state was around the corner, across the street. Then Doc sat down next to me and started playing the game. People my age didn't cruise bars, yet Luna had ensured me, so I'd given it a chance. It looked like she was right.

Touching my arm when he talked to me, angling his barstool so I was effective between his legs. Then he went to the bathroom, sliding his gentle hand across my back. When he returned, he did the same thing.

I had been on pins and needles all night, wondering if it was going to happen, if I could actually do it. This wasn't some random hookup, at least I hoped not. I liked Doc. He was interesting and funny. We both loved the Longhorns, yelling and screaming when they scored, which they seemed to do a lot this year. He made me feel like he wanted me. I guess he did. I hadn't had that feeling in such a long time.

Kickstand down, I pushed the shutoff button and pulled my helmet off, hanging it on the handlebar of the bike. "Depends. What you got?"

"You're not actually getting picky on me, are you? You've been drinking Lonestar all night. But since you asked: Crown, Jack, Macallan, and if you want real whisky, I've got a bottle of aged Jameson I keep just for special occasions."

"Special occasions. Hmmm, if I rate a special occasion, then how can I say no?"

My heart was racing so fast, I wasn't sure I was going to make it inside, but I got off the bike, turned off the ignition, grabbed my helmet and followed Doc to my fate.

To me, it was a logical choice. I wasn't what I would call gay, probably more bi-curios than anything. Sure, I'd dabbled those few times and had actually enjoyed what I'd done or had done to me. I was just lonely and tired of the dating scene. Online dating services were a waste. The women my age were all looking for someone to take care of them. I was looking for a partner, and women like that didn't use dating sites.

Besides, something (I lied to myself that it was probably Covid) had totally screwed up my hormones. My testosterone had tanked, and my estrogen was more than double what it should have been. Not only did I have boobs, but I also hadn't had an erection in over a year. The bra Doc discovered wasn't just cosmetic, it was functional, supporting a rather nice pair of modest breasts.

Women looking for partners don't go for impotent men with tits, either.

So, yeah, let's see if I could find a guy that did. I already knew I didn't have a problem with sucking a cock, and that I enjoyed being taken, so like I said, logical. It didn't hurt that Doc was taller than me, was smart, funny, good looking and so damned charming, either.

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I set my helmet on the table just inside the door and let him take my jacket, hanging it in the closet next to the table.

"Make yourself comfortable. I need a pit stop, then I'll make some drinks. It's going to be fine." I guess he could tell how nervous I was.

I just wandered. A short hallway to the right led to the laundry room and then the garage. I peeked. A sweet vintage Corvette. Just beyond that were three bikes. Damn, he rode, too.

The opposite direction led to the bedrooms. I decided that was off limits, at least for now. The big room opened up with a vast vaulted ceiling, with a large open kitchen off to my left and a massive fireplace to the right. There was another door, but it was closed and the view out the back commanded my attention, so I ignored it. The back wall was all glass, the view amazing. Doc found me out on his balcony, admiring the city. He was far enough away that the entirety of Austin spread out in front of me.

I'd never asked what he did, and he'd never offered, but it was lucrative.

"Here you go." His hand slipped in front of me with a glass of golden liquid in it, one of those golf ball sized ice cubes keeping it cold. When he pulled his hand back, his fingers traced a delicate line up my forearm.

"I like it when you do that; touch me and pretend it was an accident." He was standing right behind me. I reached back and found the hand that had just offered me the drink. Taking it in mine, I pulled it around my waist and leaned back into his chest.

For the longest time, neither of us said a word. We just stood there sipping whisky and gazing at the city.

"This. I've never done this before...with another man, I mean." I pulled his arm tighter around me, hoping I could find some strength in his embrace.

His thoughts were almost audible as he fought for just the right thing to say. "Why now?"

"It's complicated." I finished my drink and turned in his arm. "I miss the connection; the closeness, and I didn't know where else to find it." I laid my head on his chest and tried not to cry.

It had been twenty-five years since I had found 'the one.' She turned out to have serious personality disorder issues, and almost destroyed me. Somewhere in the fight to save myself, I had started cross dressing again. That just gave her more ammunition. The only good things to come out of it were my two boys, and the ten years of therapy that helped me piece myself back together. That, and the convenient coincidence that I already had bras handy when my boobs sprouted from my chest.

Just when I thought it was all coming together, Covid, shutdowns, isolation, all that crap. Now here I was, impotent with boobs, hoping some strange man I met in a bar was the answer.

Doc set his drink down and just held me, whispering soothing words while I fought back the tears.

"I should probably just go." I pulled myself free as I took a couple of deep breaths and let them out through pursed lips.

"Or you could stay and tell me all about it. Let me get you another whisky." Doc took my glass from my hand and just left me there. I wasn't going anywhere. He knew it. So did I.

I used the few minutes he was gone to regain my composure. Being in his arms had been so nice. I felt safe, accepted. He hadn't balked or freaked out when I almost lost it. He had just held me and told me everything was going to be ok. I'd believed him, trusted him.

What happened when he came back blew me away. Doc handed me my glass, walked over to the far side of the deck and pulled the cover off a hot tub. Pressing the button for the jets, he looked at me and winked. Then he stripped naked and climbed in.

"It's therapeutic. You coming?" He took a sip of his whisky and smiled at me.

I laughed and shook my head. Taking a huge sip of my drink, I went to join him, stopping as I undressed so he could see that my bra and panties matched. It was just another step in the process. Doc didn't flinch. In fact, this seductive little grin crept across his face and a sparkle caught his eyes.

"You don't have a problem with this, do you?"

"Not at all." He smiled. The look in his eyes made me shiver. "Tall and thin and you were on a bike; when I figured out you were wearing a bra, I almost attacked you right there."

I unhooked my bra and dropped it on top of my shirt and pants.

"Wait, they're..."

"I told you it was complicated." I turned around and shimmied out of the thong I had on, letting him see all of my ass. "Something messed up my hormones." I cringed as I turned around, exposing the remains of my manhood.

"And you've experimented with men. So..." He didn't have to finish the statement. I nodded and climbed into the hot water, grabbing my whisky and almost draining it.

We just talked. I told him my story. He told me his. As an endocrinologist, my current situation was of particular interest. It also explained how he had a house in the hills of Westlake. The two of us had bookmarked Earl Campbell, both missing his epic career. That put him just at seventy.

I told him I enrolled over the summer and the professor in my first class had called Earl's name. We knew it was a gag, but couldn't help but speculate that Earl probably got an 'A' regardless.

Another round of drinks and more conversation. This time, when Doc came back, he slipped into the tub next to me, wrapping his arm around me. "Tell me about the men you've been with."

"Setting expectations?" I giggled. I was just drunk enough that it seemed funny.

"Nope. I just thought they might be good stories." He kissed the top of my head and took a sip of his drink.

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"Probably not. More like a lot of disappointment. Guys I met online that I'd never pick out if I were sober. I was frustrated and curious. I figured at worst, they were proof of concept, practice. If you detach yourself from the person it belongs to, a cock isn't a bad thing to have in your mouth. If there's any kind of connection, it's actually fun. One guy I just clicked with. We talked for over an hour before we went back to my apartment. When I couldn't get him to cum, he asked if he could fuck me. I let him. He lasted another twenty minutes, and I felt things I didn't even know existed. We met up one more time and then he ghosted me. I think he was married, anyway."

"Fun. That is interesting." He let out a soft chuckle. "What else did you learn?"

"You could sit on the edge of the hot tub and let me show you." I bit my lip. I had been fondling him for the past few minutes. That fact wasn't lost on either of us. I had committed when I turned my bike off. Eager and full of anxiety and anticipation, I just did it.

Doc was almost as long as the dildo I practiced with, but thicker. I kissed the tip while my hand slid up and down the shaft. Doc leaned back and moaned when I took him in my mouth. Bobbing slowly while I played with his balls, I let his reactions lead me to where he wanted to go.

He thrust, and I took him deeper, only to pull him out of my mouth and kiss and lick my way down his shaft, ultimately taking one of his balls in my mouth and sucking on it.

Working my way back up, I smiled up at him. Feeding on the desire in his eyes; I went for broke. Relaxing, I took him back into my mouth. My tongue guided him deeper as the crown of his nob slid along the roof of my mouth and down my throat until my chin rested on his testicles.

I locked my eyes on the crystal blue of his as I slowly pulled him free. "I have this fantasy of someone fucking my throat." Licking my lips, I swallowed. Doc stood up, and I sat back, waiting for him to take control.

"You're sure." I nodded. His hands found the sides of my head and I closed my eyes, letting my mouth fall open. It was raw, primal, more intense than I thought it would be. There was no mercy in what Doc did to me. I gagged and coughed. I felt like I was going to pass out. Doc never relented. Tears streamed from my eyes. I felt his legs clench, and I knew it was time. My reward was for him to pull out and cover my face with a hot, sticky mess. I used my fingers to scrape the thick liquid sliding down my face into my mouth.

I almost didn't recognize myself. Part of me cringed with disgust at what I had just done. It was a small part, and I knew it was fleeting. A larger part felt validated, and that felt good. The rest of me, though, felt worried; worried that now that he had gotten what he wanted, Doc would send me on my way, that this was just another hookup, one more name on a too long list of disappointments.

"I didn't think you would swallow." There was genuine compassion in his eyes.

"This was better." I laughed and scooped another drop of cum from my nose, sucking it from my finger like a much smaller version of what I'd just had in my mouth.

Dunking my head under the water, I figured I could let the filter on the hot tub deal with the rest of Doc's mess. It probably wasn't the first time. If I had any say in it, it wouldn't be the last either.

"So, what now?" I got up and moved close to him, pressing my breasts into his chest. My arms slithered up his chest and over his shoulders, wrapping around his neck. I kissed him like I had kissed the girl who took my virginity; long and hard and full of everything I was feeling.

Doc's hands moved up and down my back as his kiss met mine. Our tongues fierce warriors tangled in an epic battle. When Doc's hand cupped my ass, I raised my legs and wrapped them around his waist. I had felt him growing between us. I knew the answer.

Doc turned and set me on the side of the tub. Instinctively, I laid back, pulling my knees tight against my shoulders, thanking the gods that I had played with Rodrigo just a few days ago. His twin, the dildo I practiced deep throating with, didn't rate a name. But Rodrigo, if not for Rodrigo, there would have been no way I could have been ready for what Doc did to me next.

He used his fingers to prepare me, pressing on my prostate, sending small shivers through my body. Then he took his time preparing himself. I just watched, licking my lips, letting the anticipation build as he nestled his shaft at my door. Closing my eyes, I let out a massive moan as he moved inside me. Fuck, this felt so good. I let out a soft cry as he moved deeper and deeper until he was as far as he could go.

"Are you alright?" I nodded, biting my lip, and letting the tears of joy run down my cheeks.

"Kiss me, please." It was a whimper, but it was all I had. Doc's lips met mine. I wrapped my arms around his neck and sucked his tonsils from his throat. "Now fuck me."

God, it was glorious. I didn't even know it could happen, but my flaccid little soldier spewed hot sticky mess all over my stomach, twice, while Doc pummeled my eager ass. The feelings tearing through me were so far beyond anything I'd ever felt; I knew in my soul this was the way it was supposed to be.

Buried deep in my bowels, Doc shuddered and trembled as he pulsed inside me.

"Oh fuck, oh shit, oh fuck, that was incredible. I didn't know it could feel like this." I grabbed Doc and pulled his lips to mine again, wrapping my legs around him and using my feet to keep him as far inside me as I could.

"Eric." Doc started laughing. "You need to let me go."

"Don't want to." I started laughing, too.

"My legs are cramping, please." I relaxed and slipped into the water, cleaning the mess off my stomach while Doc climbed out and gathered out clothes.

"Come rinse off with me. We're meeting some friends for breakfast and then a ride in the morning. We need to get some sleep." Just like that, Doc and I were 'we,' and he was in charge.

Showering together was just another level of intimacy. I explored his body, and he explored mine. It was just one more piece of the puzzle we were building together, just one more facet to the gem. One more aspect of this strange and wonderful new relationship I had found.

The entire evening had been like slowly sinking into a nice hot bubble bath; warm and soothing, comfortable, the aches and pains slowly dissipating amidst the bubbles. Meeting Doc, letting him seduce me, because that's what he did. Sure, I knew it and was a willing participant, but he still played me to where my surrender was inevitable.

The most powerful form of seduction is to give the person exactly what they need. What I needed more than anything was to be close, connected, intimate with someone.

The closer I got to him, the closer I let him get to me, the more complete I felt. Him wrapping me in his arms as I drifted off to sleep; I had never felt this safe.

***

The morning found me strangely content. I guess I had rolled on my back and splayed out, taking up an inordinately large amount of the bed. Something felt nice. Gentle caresses sending shimmers across my skin as I slowly awoke. Moaning softly, I opened my eyes. Doc was touching me, running his hand over my body. He caressed my modest breasts and then my waist and hips, finally fondling me a little.

"Hey." I smiled at him. "Having fun?"

"A little." He smiled back and leaned down to kiss me. "I like boys like you. Usually they're a lot younger, but tall and thin just does something I can't describe to me. That you ride a bike and can have an actual conversation is nice, too."

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