Sex encounters with married or older guys

I was in a laundry room in my first apt building. I was 23.

The Persian building manager (who lived upstairs with his wife and toddlers) came in. It was late and he told me the laundry door is usually locked by 11pm. He said “you are new?”
I said “yes, apt 101. Under yours. Your wife was very nice when I did the application. “

I told him my name. He smiled like he was amused by me.

He was probably age 39-40 dark haired, tall, strong build but a sexy daddy paunch and I loved his hairy forearms. His sleeves were rolled up. His hands were big.

I extended my hand. He took it and sorta pulled me over to him. A hand shake but a power play I guess. He was taller than my 5,7 frame. He stared down at me.
He said, “ you have a boyfriend upstairs?”
I felt suddenly even more feminine than my usual gay ass self. I shyly said, “no. “
He let go of my hand and said “ok”.
He said good night and said that he’s down here every night at 11pm to lock up. “ I’ll see you.”

I felt an excitement down my spine to my pussy ass. I went back to my apartment and rubbed one out on my bed, hoping he’d hear me.
OMG sooooooooooo hot
 
  • Like
Reactions: ZeldaZonk
From The King to The Alpha Boss

I was feeling unsettled that Friday nights.
After 7 months with my Haitian King, he was becoming too busy with work to have me over, or he was fucking that office redhead chick who was all over him at the Summer office picnic. We had previously not gone 2 days without him at least using my mouth and now it was 4 days since I’d been in his bed.

When a sissy sub bottom is pushed aside or loses his Dom Top, it’s a fall from grace that is profoundly upsetting. It’s like an air hunger of a drowning man. Our body hungers for their taste, scent, touch, voice - any connection.
I was showered, pre-lubed, in a jock under my slacks, and wearing my clitty cage as I drove to his house that Thursday and was like an addict desperate for a fix. He called my cell as I drove closer to his neighborhood. He was on deadline for work, and he needed tonight to focus. Stay home. I started crying and he hung up. I pulled over and screamed (dramatic I know) and I unlocked my clitty cage and threw it out the window into an empty lot.

For the first time, I considered running over to the old apartment to see The Persian but I was afraid. Afraid of how the King would react if he found out later once (if?) things got better between us - and afraid the Persian would spit in my face and kick me out. Sometimes sexy memories are better left alone.

There was a corporate party coming up the next night, Friday night. It was the King’s company’s fiscal year-end party at a trendy bowling lanes/lounge and karaoke club. The King had invited me weeks earlier when we were ok. Maybe he didn’t expect me to show up. I would be there.

I arrived an hour into the party. My Uber took longer. I was wearing a lace thong under my linen pants and my ass looked nice. The party was in full bloom. Interns and VPs alike were getting libricated on the free cocktails and minimal pass around food, sliders and pizza.
I was expecting to be fucked deeply so I had been maintaining my diet and hygiene in prep for this all week. No food for me. I had a wine.

I found The King in the karaoke room. His VP status and big ego and big sexy body made him magnetic to the bros and ho’s. The redhead bitch was laughing at his joke too loudly.

He saw me walk in and shot out of his seat,
He walked me over to the men’s room area that was quieter. “You invited me” I defended myself but shaky and scared he was mad.
“I haven’t seen you all week. Please. Tonight just us.” I whined. He told me had plans and I needed to go. I went into panic mode, I started suggesting anything he might like. “Let’s get the sling room at the bathhouse. You can do anything you w—“. He grabbed me arm. My voice cracked and my tears welled up.
He bent over me and sternly said, “Don’t you DARE start crying.”

At that moment his Boss came out of the men’s room. I saw my King flinch and try to compose himself.. I could see in that moment that King was not the top dog at the company as he insinuated. The Boss barked “Everything alright here, fellas?” The Boss stared at me and back at King. King said, “this is my roommate.” I shook the Boss’s hand and I thought my fingers would break. He laid it on thick. He and The Boss made small talk. I checked out The Boss.
He was 50-something short solid Latino with grey hair leaking out from his black goatee. His head was shaved. He looked great in a sports coat with unbuttoned shirt. “I won’t be staying much longer”, The Boss said. He told us to have fun and nice meeting me. I nervously said you too. He was commanding. Master and commander - I found out later he had been a Marine.

Soon after, having been dismissed and led to the exit by King, I was in an emotional state.
This might be a phase I hoped, but then I panicked at the idea I would never feel him in me again. Maybe he was with the girl now.

As I awaited the return uber, a voice from a Mercedes in the valet lane yelled to me.
“Hey you need a ride?”

The Boss was in the driver’s seat.
His jacked was off- his sleeves were rolled up.
His muscled forearms looked good.
I hesitated for a second, then my beta response kicked in. “Sure!” I got in and we rode off.

My wild night was just beginning.
 
From The King to The Alpha Boss

I was feeling unsettled that Friday nights.
After 7 months with my Haitian King, he was becoming too busy with work to have me over, or he was fucking that office redhead chick who was all over him at the Summer office picnic. We had previously not gone 2 days without him at least using my mouth and now it was 4 days since I’d been in his bed.

When a sissy sub bottom is pushed aside or loses his Dom Top, it’s a fall from grace that is profoundly upsetting. It’s like an air hunger of a drowning man. Our body hungers for their taste, scent, touch, voice - any connection.
I was showered, pre-lubed, in a jock under my slacks, and wearing my clitty cage as I drove to his house that Thursday and was like an addict desperate for a fix. He called my cell as I drove closer to his neighborhood. He was on deadline for work, and he needed tonight to focus. Stay home. I started crying and he hung up. I pulled over and screamed (dramatic I know) and I unlocked my clitty cage and threw it out the window into an empty lot.

For the first time, I considered running over to the old apartment to see The Persian but I was afraid. Afraid of how the King would react if he found out later once (if?) things got better between us - and afraid the Persian would spit in my face and kick me out. Sometimes sexy memories are better left alone.

There was a corporate party coming up the next night, Friday night. It was the King’s company’s fiscal year-end party at a trendy bowling lanes/lounge and karaoke club. The King had invited me weeks earlier when we were ok. Maybe he didn’t expect me to show up. I would be there.

I arrived an hour into the party. My Uber took longer. I was wearing a lace thong under my linen pants and my ass looked nice. The party was in full bloom. Interns and VPs alike were getting libricated on the free cocktails and minimal pass around food, sliders and pizza.
I was expecting to be fucked deeply so I had been maintaining my diet and hygiene in prep for this all week. No food for me. I had a wine.

I found The King in the karaoke room. His VP status and big ego and big sexy body made him magnetic to the bros and ho’s. The redhead bitch was laughing at his joke too loudly.

He saw me walk in and shot out of his seat,
He walked me over to the men’s room area that was quieter. “You invited me” I defended myself but shaky and scared he was mad.
“I haven’t seen you all week. Please. Tonight just us.” I whined. He told me had plans and I needed to go. I went into panic mode, I started suggesting anything he might like. “Let’s get the sling room at the bathhouse. You can do anything you w—“. He grabbed me arm. My voice cracked and my tears welled up.
He bent over me and sternly said, “Don’t you DARE start crying.”

At that moment his Boss came out of the men’s room. I saw my King flinch and try to compose himself.. I could see in that moment that King was not the top dog at the company as he insinuated. The Boss barked “Everything alright here, fellas?” The Boss stared at me and back at King. King said, “this is my roommate.” I shook the Boss’s hand and I thought my fingers would break. He laid it on thick. He and The Boss made small talk. I checked out The Boss.
He was 50-something short solid Latino with grey hair leaking out from his black goatee. His head was shaved. He looked great in a sports coat with unbuttoned shirt. “I won’t be staying much longer”, The Boss said. He told us to have fun and nice meeting me. I nervously said you too. He was commanding. Master and commander - I found out later he had been a Marine.

Soon after, having been dismissed and led to the exit by King, I was in an emotional state.
This might be a phase I hoped, but then I panicked at the idea I would never feel him in me again. Maybe he was with the girl now.

As I awaited the return uber, a voice from a Mercedes in the valet lane yelled to me.
“Hey you need a ride?”

The Boss was in the driver’s seat.
His jacked was off- his sleeves were rolled up.
His muscled forearms looked good.
I hesitated for a second, then my beta response kicked in. “Sure!” I got in and we rode off.

My wild night was just beginning.
OMG sooooooooooooo hot
 
  • Like
Reactions: ZeldaZonk
The Boss drove me to the apartment.

I spent enough time with King that I had been given a key - but with strict instructions to call first and not come unannounced. I kept my little studio across town but hadn’t been there much in the last 7 months.

King had enjoyed telling his co-workers that I was his roommate. Maybe it made him seem cool to be buds with a little sissy like me.
With The Boss I continued the charade. I figured I could get at least a ride over there before King and his office slut left the party and I could snoop around his place. Maybe I’d steal his underwear as a keepsake. It seemed final.

The Boss asked me if I knew who he was.
I said that I’d been to the summer employee picnic. “You’re the big Boss.”

He smiled. “I’m CEO. Yah the big boss.”

I was starng at his strong arms steer and drive and his watch looked good on his arm. He had a tattoo on his forearm.

“I like your tattoo.”

He told me it was a leftover from his time in the Marines in his twenties. I told him I was impressed.

It’s hard to explain the magnetic way that a femboi can find the most masculine alpha men in his path. Or maybe they draw me in? Since age 19, I’d met a few military, ex-military and law enforcement. I loved their energy and how they fucked. They never apologized or had a bit of guilt for wanting to use a sissy like me. They felt entitled. I believed in my soul they were. They deserved the worship. The chemistry was off the hook.

The Boss pulled up front and said he’d go in with me. “I need to take a leak but it’s early and I have time for a beer. That cool?”
I nodded, ok.

We walked into King’s apartment and he went to the bathroom. He left the door open to piss which I found strange but sexy.

I looked around the place for any evidence of my panties or the other girl in King’s life.
The Boss came out of the bathroom holding the dog leash. It was what King put around my neck. We’d been doing that for months.
“Where’s the dog?”

My mind reeled to try to explain this shit.
“he was dog sitting last week, but it’s gone home.”

He looked into the one bedroom.
“Tight quarters, huh?” He asked sarcastically knowing full well I was in the bed too.

I said that I’d been sleeping on the couch.

The Boss gave me a look. He walked up to me with the leash in his hand. “Look here, Princess. Don’t lie to me. I raised 2 kids and I know when I hear bullshit.”

I was getting scared. Being called Princess was new and it sounded good. It was different - but it said a lot. His being a father of two adult kids was sexy to me as well. I was still nervous as to where this was going.

He told me to sit down on the sofa and he sat next to me. “Let me ask you this? You two seemed to be not hitting it off tonight. Are you happy here?”

I shook my head. “No, sir.”
I added the Sir to see how he’d respond.
His eyes lit up. He liked it.

He got up and walked to the kitchen.
“When my kids didn’t appreciate their toys, I would go in and take it all away. They have to learn to appreciate nice things.”

He looked under the sink and found trash bags. He threw 2 Hefty bags in my lap.
“Gather all your shit. Anything that was yours.
You can come to my place tonight. Sound good, Princess?”

It certainly did. I guess I was the “nice thing” he was taking away from his hot shot employee.

I packed up any of my clothes, robe, lotions, thongs and fishnets, the leash, butt plug and nail polish and lipstick from King’s medicine cabinet. I left my door key on his dining room table and walked out with The Boss.
In the last two years with 3 men, I’d gone from “cocksucker/ bitch” to “sissy cunt” to “Princess.”
Life was full of surprises.
 
When you’re a sub bottom who falls for the older Alpha man, you become even greedier for their passion. You think of the decades that you missed out on. The years of your childhood when they were studs fucking like young bulls. Your soft smooth flesh and welcoming ass and mouth fuels their fire once again and you get a glimpse of the full man, past and present. You drink them like fine wine. You want them to pour their life experience, all the joy and all the rage into you. You lie next to them and feel more complete. They treasure you - but you are the one who is transformed. You become more of your authentic submissive (feminine) self. You are born. They gave you life.
 

Attachments

The Boss drove us across town. We were further out than I thought. When he relaxed his arm on the console I was compelled to touch his bicep.

“We’ll be home soon, Princess. My kids are across the country in college and my wife stays in Mexico. I have the place to myself until the housekeeper comes Monday afternoon.”

He was drinking a big water he’d pulled from his trunk - when he’d thrown my trash bags of clothes, sex toys and lingerie from my exes.

“I want to make you happy, Sir.” I said in my femboi way.

“Get undressed. Now. Get it all off”
He commanded.

I stripped shirt slacks and shoes and removed my thong. He glanced at my crotch.

“I’m not caged, I’m sorry.”

“No problem, Princess. You are fine as is.

We pulled into his garage. The house was big. I guessed maybe 5 bedrooms / 3 baths.
The garage was big with a section for 2 cars and an area for a pool table.

He told me to wait. He went inside, turned on some lights, opened my door and said get out.
As we approached the threshold, he said “get down.” Pushing me to my knees, he said I had to crawl into his home.

I followed him crawling down a hall. The marble floor was cold and hard on my knees.
“Right this way, Princess.”

We walked through a small first floor bedroom with an en suite bathroom. He told me to get in the clawfoot bathtub. He told me to stay and walked out.

I kneeled in the tub wondering what was going to happen. 15 minutes later he walked back in wearing a wifebeater and boxers. Fuck! He had a sleeper body. I didn’t know his military build would be so sexy at age 51. His armpits were black and wild. His legs firm and hairy.
He approached the tub, and took out his cock.
It was short and thick. 6x8 I guessed. Beer can thick.

“Big Boss.” I said looking up.

He was very serious and didn’t smile. He started pissing on me. First he hit my chest and slowly the stream lifted to my chin. I was game and dipped down to catch a splash in my mouth. He redirected and let it go. I gargled with it and spit it out. Over and over.
I let it wash onto my shoulder length hair.
If this was his thing I was going to show him I loved it. It was some Baptism by piss or him marking me as his bitch. It was fine by me.

When the stream ended. He turned on the shower. The cold water that hit me was a shock and I really hated it but he liked seeing me adapt for him. He toweled me off, took me out and had me crawl into the bedroom.

He put a robe on me then sat on the small sofa next to this guest room bed. He told me to come up and he scooped me. I was in a robe in The Boss’s arms.

He had a beer on the side table and drank it.
He spoke to me in hush tones even though we were alone.

“Are you glad you came home with Dad?”
yes
“You’re safe with Dad.”
Thank you Sir
“You like Daddy’s beard?”
Yes, Sir. May I touch it ?
“Yes, Princess”
I stroked that fur and leaned in for a kiss.
He gave me a firm but tender kiss.
“You my Princess?”
Yes daddy sir.

This tenderness went on for a while. I stroked his muscular arms and put the end of his silver chain’s holy medal in my mouth. I wanted to taste him.

I want to suck your cock, sir.

He had other plans.
I was back in the tub for round 2 of piss and water shock.

We eventually got around to the cocksucking.
He guided me to tongue and suck it just as he wanted. I learned fast and he was happy.
He was firm but wasn’t a brutal facefucket and he let me enjoy it and he kicked back sipping his beer and watching my progress.

I hadn’t eaten properly in days, Dad’s salty cock and cum we’re going to have to suffice because I was keeping my pussy ass ready.

He said he was gonna shoot and told me to stick my tongue out. He wasn’t going to let me swallow his cock. He had to let it sit there on my tongue.

“Hold it”
“Wait”
“ok”
And I was allowed to swallow.
It was one of many commands he would teach me to obey. “Knees” “Crawl” “hold” were a few I’d learned the first day.

My pussy ass was twitching. I wanted this man to fuck me.

He told me it was time for bed. He took off my robe and put me in the guest room bed.
He kissed me good night.

“We have all day tomorrow if you want to stick around here.”

I told him I wanted nothing more than to be here.
 
I was in a laundry room in my first apt building. I was 23.

The Persian building manager (who lived upstairs with his wife and toddlers) came in. It was late and he told me the laundry door is usually locked by 11pm. He said “you are new?”
I said “yes, apt 101. Under yours. Your wife was very nice when I did the application. “

I told him my name. He smiled like he was amused by me.

He was probably age 39-40 dark haired, tall, strong build but a sexy daddy paunch and I loved his hairy forearms. His sleeves were rolled up. His hands were big.

I extended my hand. He took it and sorta pulled me over to him. A hand shake but a power play I guess. He was taller than my 5,7 frame. He stared down at me.
He said, “ you have a boyfriend upstairs?”
I felt suddenly even more feminine than my usual gay ass self. I shyly said, “no. “
He let go of my hand and said “ok”.
He said good night and said that he’s down here every night at 11pm to lock up. “ I’ll see you.”

I felt an excitement down my spine to my pussy ass. I went back to my apartment and rubbed one out on my bed, hoping he’d hear me.
That is hotttt
 
For the next year I was his bitch.
Having him walk into my place just downstairs from his sleeping family and use my holes was incredible.

He taught me quickly about not touching my self and letting the anal be enough. It was.

He brought me my first lace black
Thong to wear and I loved it.

He called me his “panty boy.”

The one glorious time his wife and kids went away to visit her mom in Texas was incredible.
He fucked me as hard and we were as loud as can be. Nobody upstairs to hear and being an end unit gave us that privacy.

I sucked him on my balcony. Lights off,
Super hot.

One messy memory was the time wifey was in bed and I was below his balcony on mine.
He smoked his cigars and I would often insert butt plugs and look up at him. He surprised me that one night by switching his light off and pissing down on me in my Lawn chair. You know I loved it. He was getting more audacious and risky.

It ended when after a year I had my eye on this sexy black guy down the street and started spending time there. Yes my slutty hunger for alpha cum made me stray from The Man.

I moved out not long after. I’m sure my sexy Man will be finding panty boy tenants as long as he manages buildings. He was so naturally macho and sexy, he will be turning gays into femboys for married men well into his sixties I imagine.

I still think of him.
You are soo lucky mmmmm wow
 
The next morning I awoke at 5am and crawled into the bathroom (still following his rules) and stood up to rinse my mouth with mouthwash and brush my teeth with the new toothbrush left for me in the guest bath. The toilet had a bidet so my hole was minty fresh too.
I went back to bed hoping The Boss would come down and fuck me. I fell back asleep and awoke to the sound of The Boss walking onto my room. He sat at the edge of my bed in nylon shorts and Tshirt. He brought me a smoothie and told me I should take a nice bath while he was upstairs working out. He gave me a kiss and his tongue was thick and I caressed it, sucking it in my mouth. I reached for his fat cock. ( his 6X6 beer can hammer - sorry for typo earlier). He said “get ready for daddy and I’ll be back down in about 90 minutes.”

I found out he worked out at home on weekends. His home was his castle and he wanted privacy from the outside world when he left the office on Fridays.

I was ready when he came back in shirtless, glistening with sweat and looking like a man possessed. He turned me around on the bed pushing me flat and my head tipped over the edge. He wanted my throat.

He was ripe as fuck and still dripping sweat.
His body looked so good and his pecs and shoulders were popping. I was really hungry for him.

He heard me gag and choke and told me to relax and go easy. You can have this all day.

He climbed on me and I wrapped my legs around him. I felt his heart pounding and his back felt so proud and slippery and I was really feeling happy he chose me. His kisses were deeply passionate now, teasing, I teased back, biting his lip gently. He got off walked into the bathroom and under the sink he pulled out some wrapprd MAGNUMS. He eagerly wrapped his thick head with the condom.

“Please daddy, fuck em raw. I need to feel just you.”

He replied, “Be patient, Princess. That will happen.”

He grapped my ankles and pulled me up and he guided his cock against my tight hungry pussy ass. With one strong thrust, he burst into me. There was no easy does it. He piled drove it in. I gasped, my eyes looking at him in shock.
Fuck! He was thick. My pussy hadn’t felt cock in a week and I was in heat. I breathed through the initial pain and immediately found myself pushing back. We worked up a rhythm. No speaking just staring at each other and kissing. and fucking like animals.

Maybe it was deep desire to be back in a man’s good graces or my love of his cock filling and stretching me - but this felt really good.

I cried out, oh daddy it’s making me-
And my clit shot out a rope of cum on my belly.
Oh my god, assgasm right from the start.
I reached around his back and dug in my nails.
He said, “scratch me Princess. Scar me up.”
This sexy fucker. 61 and fucking like a bull.

“Oh fuck”. He was getting close and he wanted me on my stomach. He dove into me and came deep. I prayed the condom was busted and I would feel his fire inside.

When we recovered and he peeled off the condom it was loaded with seed.

He didn’t have to say anything. My tongue was out and he poured all over me.

“Hold”

“Hold”

“Hold”

Ok- now

I swallowed.

He took me upstairs to his shower where I sucked and took piss.

I spent the day with him and the next.
And the following weekend I had been tested and was HIV negative and put on prep.
He said I needed to wait another week to get him bareback. I was counting the days.
 
My first breeding by The Boss

The Boss and I had spent some quality time together. He had driven me to my small studio and had me pack up my best lingerie and clothing. He picked me up from my retail job at the MAC counter each night at 7:30pm.
His housekeeper and cook left meals to reheat or finish up on M, W, Thurs. Weekends were ours. He took a break from CEO demands for all of Saturday, and Sunday he dipped his big toe back in by reading all the financial news, and newspapers and checked email. He would throw me the celeb news and broadway theater sections that I liked.

He liked an extra long sucking by me on Sundays when he watched football. I would pour his whiskeys (he only had two) and nestled between his big thighs. Sometimes he would feed me his big foot and I would suck.
When he placed his sole on my face and lightly pushed me backwards it was a turn on.

I had learned that his kids were 19 and 21 just a few years younger than me. His wife was permanently in Mexico. It was a ‘cheaper to keep her’ situation and she was happy in her homeland and took their beach condo as her year round home. It would be a permanent separation. He had married a pretty girl from Manzanillo. He grew up in Texas and he did everything society told him to do after the military career. Now The Boss was 61 and busy with his own company and needed his rules and only his needs met. I was more than happy to be his boi wife or whatever he wanted to called it.

He had asked me to consider quitting my job in retail and he would pay me as an assistant on his company payroll. I’d run errands and pickup his dry cleaning and buy staff gifts as needed. I said I would like that but I wasn’t yet ready to say goodbye to the girls and gays I worked with as we enjoyed our job.

The Boss liked my finger nails painted red and my toe nails pink. He took me into his wife’s closet and told me I could have anything she had left behind. I found some nice silky robes and stockings that I’d wear at night for The Boss. At this point, I was still sleeping and getting fucked in the guestroom downstairs.

My “probation” period was over and I had been taking my prep pills for 10 days. The Boss said he wanted to take me to dinner. We went out to his favorite Mexican restaurant. I had light fare and hoped that this would be night we took off the Magnums.

He brought me home and we kissed in the living room. He told me that I was his now and he wanted me to stay. I told him I wanted to be with only him and promised to obey.
He carried me upstairs and undressed me.
We were in his King bed and I was thrilled.
He stripped and I zeroed in on his tattoo across his belly. I had memorized every line and traced it again and again with tongue the last 2 weeks. He told me he had taken a Cialis pill after dinner as we left the restaurant.

The Boss fucked me for 6 hours, ass to mouth to ass to mouth. My pussy was red and gaped and sore. He went downstairs and told me to put ice on it. I iced it while he kissed me and I kissed his chest. I was really falling for him.
I had never met an Alpha who was passionate and dominated me so naturally and tenderly as needed.

When he was ready to shoot I was on my back with arms wrapped around him. His silver cross on his neck dangled between us. I had dug my nails into and clawed his back as he wanted. I felt the electric jolt in my ass and my clitty dribbled out more of my juices that I’d been cumming for hours. The assgasms were plentiful.

“YOU. FUCKING. HOT. CUNT!! ” He yelled and shot loads into me. He moaned and moaned.
I welcomes his liquid fire and cried out of excitement and relief that he had finally let go in me. We laid there to recover and he rolled
over to check on me and wiped my tears away.
I got the most amazing kiss and his tongue was so warm and delicious I wanted to cry again.
“Your pussy is so succulent. My God!”
I plugged myself to keep his seed in me, and then laid my grateful head on his belly to sleep.

I was home.
 

Attachments

Epilogue:
The night he took me home from the party we had removed the sex toys and dog leash from the Haitian Bull’s place.

The Haitian had texted me days later but I didn’t reply. This was The BOSS’s employee and I didn’t want to upset The Boss.

I learned that if I told The Boss any lie and he found it I would be getting 20 whips with his belt across my ass. I was careful to tell the truth.

The Boss told me later that he had called The Haitian Bull VP into his office that Monday morning after my first weekend as The Boss’s suck boi.

The Boss had discussed a potential promotion and piled on a new client and deadline. As they wrapped up The Boss took out the leash from his drawer and laid it on his desk. My leash! The leash that the Haitian Bull had used on me. The Boss told him
“I PIcked up a stray the other night. She’s proving to be very good girl.”

The closeted Haitian Bull looked at the leash in disbelief and panic. The Boss said he could leave, “you have a lot of work to do.”
 
Well, to start, I am an older married man and I have some experience with younger men (younger than me) as well as with men older than me. Some of them have been married and some not.

I had been very bi-curious for quite some time, and that combined with the fact that my wife was becoming less and less interested in sex, I had strong urges for something more than just jacking off. I have always enjoyed jacking off, so that was not a bad thing!

I was on-line one day chatting with a guy. We had been chatting off and on for some time, each of us in a similar situation regarding sex at home with our wives. We would talk about our interests and both of us had been thinking about what it might be like to stroke another man's hard cock, or maybe even suck some cock. Our conversations got pretty hot and we would jackoff while we chatted.

We started to exchange some pics of our cocks as we stroked them during our chats. We talked about how we liked each other's cock. We both preferred cut rather than uncut. Mine was a bit larger than his, but his was a very nice shape and I liked how it looked.

One day he commented how he was so turned on by our conversations and wished that we could do more than just chat. He said he liked my cock very much and would love to be able to play with it. I agreed with him and said it would be great to get together. He said something about wishing were lived near each other and he would definitely get together.

I realized at that point that we had never asked about where we lived, So I asked him, and I was very surprised to find that he lived in a town only 30 minutes from my house. Just after he said where he lived, I told him where I lived and I said we needed to give this a shot.

We set a day and time the following week. He and his wife were both retired, and he said he could tell his wife he was going for a ride. He said that he liked to take afternoon rides on his Harley. I told him that both my wife and I were still working, and that while she went to work everyday, I worked from my home office, thus we set it up for him to come to my place.

When the day arrived, we checked on-line to make sure everything was still on, and he said he would be leaving shortly. I went down to my garage and opened the garage door. I was going to have him drive right into the garage and i would close the garage door, so no one would even know he was there.

I stood at my back door, which led into our kitchen from the garage, waiting for him. I was getting hard from the anticipation. He arrived, I waved him into the garage and I closed the door behind him. He came into the kitchen and at first we just stood there talking. I then said that if we were going to do this we should just start.

I undid my pants, took them off, along with my underwear and was standing in front of him with my cock getting harder by the second. As I stood there playing with my cock, he took off his pants and started dong the same. He seemed very nervous, and we were both very obviously excited.

I then reached out and put my hand on his cock. I started stroking his cock as I continued stroking my own as well. I could tell by his reaction that he liked having me stroking his cock. After a few minutes of stroking him, he reached over and started stroking my cock. It was the first time for each of us, having another man stroking our cocks. (I did have a brief experience with another boy when I was 13, but nothing since.)

We had both talked about wanting to try sucking cock when we were chatting on-line, so I said that if I was going to try it, then I should just get to it. I just leaned over and put his cock into my mouth. Like I said, he was not as big as me, maybe 5 inches, and so I was able to take his entire cock into my mouth. The first thing I noticed was that it did not feel weird, but rather felt very natural. The hardness and yet the softness was something I noticed.

He almost collapsed when I took his cock into my mouth. I started sucking and licking and it took less than a minute and he was ready to cum. I could feel that he was close and I kept his cock in my mouth when he said he was going to cum. He started cumming and I swallowed every drop.

That was my first experience with stroking and sucking another man's cock. Since then I have met up with several other guys. We have jacked off together, jacked each other off and done some sucking. Some of these guys were my age, but some were younger, and all but one was married. The man that was not married is the only guy that said he was gay. He is also the only one to suck me to completion and swallowed my load.

There was a younger man, around 35, that I have gotten together with the most. By the way, I was 64 when I sucked that first cock several years ago. This younger man came to my house the first time and he had not done anything with a guy before. he was married and had a good sex life with his wife, he was just curious about doing something with guys.

The first time he was at my house, all that he did was get naked, watch porn and while he stood in front of the chair where I was sitting, I jacked him off. He has a very nice looking cock, almost as big as mine. I have referenced these other cocks not being as big as mine, but I should state mine is not huge, but I am above average in length and girth.

The next time the younger man came to my house we both got naked, sat on the sofa watching porn and I started stroking his cock right away. He did let me suck him for a little bit, but did not want to cum in my mouth, so I stroked him until he came, then I jacked myself off as he watched.

He and I have gotten together more at my house and his, he has gotten much more comfortable and now will suck my cock as well as stroke me. I have sucked him off a few times and swallowed. He has also shown me some videos of his wife. She is a bigger girl, but very pretty and very sexy. Watching her masturbating for him on video was very hot.
 
Well, to start, I am an older married man and I have some experience with younger men (younger than me) as well as with men older than me. Some of them have been married and some not.

I had been very bi-curious for quite some time, and that combined with the fact that my wife was becoming less and less interested in sex, I had strong urges for something more than just jacking off. I have always enjoyed jacking off, so that was not a bad thing!

I was on-line one day chatting with a guy. We had been chatting off and on for some time, each of us in a similar situation regarding sex at home with our wives. We would talk about our interests and both of us had been thinking about what it might be like to stroke another man's hard cock, or maybe even suck some cock. Our conversations got pretty hot and we would jackoff while we chatted.

We started to exchange some pics of our cocks as we stroked them during our chats. We talked about how we liked each other's cock. We both preferred cut rather than uncut. Mine was a bit larger than his, but his was a very nice shape and I liked how it looked.

One day he commented how he was so turned on by our conversations and wished that we could do more than just chat. He said he liked my cock very much and would love to be able to play with it. I agreed with him and said it would be great to get together. He said something about wishing were lived near each other and he would definitely get together.

I realized at that point that we had never asked about where we lived, So I asked him, and I was very surprised to find that he lived in a town only 30 minutes from my house. Just after he said where he lived, I told him where I lived and I said we needed to give this a shot.

We set a day and time the following week. He and his wife were both retired, and he said he could tell his wife he was going for a ride. He said that he liked to take afternoon rides on his Harley. I told him that both my wife and I were still working, and that while she went to work everyday, I worked from my home office, thus we set it up for him to come to my place.

When the day arrived, we checked on-line to make sure everything was still on, and he said he would be leaving shortly. I went down to my garage and opened the garage door. I was going to have him drive right into the garage and i would close the garage door, so no one would even know he was there.

I stood at my back door, which led into our kitchen from the garage, waiting for him. I was getting hard from the anticipation. He arrived, I waved him into the garage and I closed the door behind him. He came into the kitchen and at first we just stood there talking. I then said that if we were going to do this we should just start.

I undid my pants, took them off, along with my underwear and was standing in front of him with my cock getting harder by the second. As I stood there playing with my cock, he took off his pants and started dong the same. He seemed very nervous, and we were both very obviously excited.

I then reached out and put my hand on his cock. I started stroking his cock as I continued stroking my own as well. I could tell by his reaction that he liked having me stroking his cock. After a few minutes of stroking him, he reached over and started stroking my cock. It was the first time for each of us, having another man stroking our cocks. (I did have a brief experience with another boy when I was 13, but nothing since.)

We had both talked about wanting to try sucking cock when we were chatting on-line, so I said that if I was going to try it, then I should just get to it. I just leaned over and put his cock into my mouth. Like I said, he was not as big as me, maybe 5 inches, and so I was able to take his entire cock into my mouth. The first thing I noticed was that it did not feel weird, but rather felt very natural. The hardness and yet the softness was something I noticed.

He almost collapsed when I took his cock into my mouth. I started sucking and licking and it took less than a minute and he was ready to cum. I could feel that he was close and I kept his cock in my mouth when he said he was going to cum. He started cumming and I swallowed every drop.

That was my first experience with stroking and sucking another man's cock. Since then I have met up with several other guys. We have jacked off together, jacked each other off and done some sucking. Some of these guys were my age, but some were younger, and all but one was married. The man that was not married is the only guy that said he was gay. He is also the only one to suck me to completion and swallowed my load.

There was a younger man, around 35, that I have gotten together with the most. By the way, I was 64 when I sucked that first cock several years ago. This younger man came to my house the first time and he had not done anything with a guy before. he was married and had a good sex life with his wife, he was just curious about doing something with guys.

The first time he was at my house, all that he did was get naked, watch porn and while he stood in front of the chair where I was sitting, I jacked him off. He has a very nice looking cock, almost as big as mine. I have referenced these other cocks not being as big as mine, but I should state mine is not huge, but I am above average in length and girth.

The next time the younger man came to my house we both got naked, sat on the sofa watching porn and I started stroking his cock right away. He did let me suck him for a little bit, but did not want to cum in my mouth, so I stroked him until he came, then I jacked myself off as he watched.

He and I have gotten together more at my house and his, he has gotten much more comfortable and now will suck my cock as well as stroke me. I have sucked him off a few times and swallowed. He has also shown me some videos of his wife. She is a bigger girl, but very pretty and very sexy. Watching her masturbating for him on video was very hot.
Nice story! What about penetration? Did that occur?
 
For the next year I was his bitch.
Having him walk into my place just downstairs from his sleeping family and use my holes was incredible.

He taught me quickly about not touching my self and letting the anal be enough. It was.

He brought me my first lace black
Thong to wear and I loved it.

He called me his “panty boy.”

The one glorious time his wife and kids went away to visit her mom in Texas was incredible.
He fucked me as hard and we were as loud as can be. Nobody upstairs to hear and being an end unit gave us that privacy.

I sucked him on my balcony. Lights off,
Super hot.

One messy memory was the time wifey was in bed and I was below his balcony on mine.
He smoked his cigars and I would often insert butt plugs and look up at him. He surprised me that one night by switching his light off and pissing down on me in my Lawn chair. You know I loved it. He was getting more audacious and risky.

It ended when after a year I had my eye on this sexy black guy down the street and started spending time there. Yes my slutty hunger for alpha cum made me stray from The Man.

I moved out not long after. I’m sure my sexy Man will be finding panty boy tenants as long as he manages buildings. He was so naturally macho and sexy, he will be turning gays into femboys for married men well into his sixties I imagine.

I still think of him.
Are they you guys?