April 2025 -- Office/Boudoir
We bought this big ass house on the golf course for several reasons. It was a hell of a deal frankly, 9,000 square foot Mediterranean on 1 ½ acres, outside gallery surrounding the house on both first and second floor, which we thoroughly enjoy. My wife and I could take our private golf cart out to play the course anytime we wanted. The swimming pool area and the landscaping were incredible and well maintained. It was a great deal.
But the house was dated; it needed to be modernized, hence the great deal on the purchase price. So, every year my wife undertakes a modernization project for the spring and there are carpenters, electricians, plumbers, painters and the like all over the house taking care of her whims and wishes. Couple rooms at a time.
Well, so far my wife’s projects have not interfered with what I call “my side of the house.” Although we still love and cherish each other, we spend the day living fairly separate lives. We have three meals a day together and sleep together, but otherwise, I’m up in my “office/study/library/man-cave” on the computer and phone, managing our businesses, or I’m watching porn, or if I’m lucky, I’m sucking cock or getting fucked by a big, hard cock.
For those of you who know us, you know my wife and I have been active bisexual swingers since before we were married 50 years ago. We both loved pussy and cock until 2010 when menopause did more than just “pause” her sex life; it ended it. Well, her desires haven’t stopped me, although I haven’t had pussy since 2009, and that’s fine with me, and she’s good with that as well. What she’s not exactly crazy about is that I’m more of a sissy f.a.g.g.o.t than I’ve ever been and I spend the days in my upstairs office/boudoir if you would, dressed in the finest lace and fishnet and lingerie that can fit a 6’6”, 250 pound athletic, trim, and fit old queer.
The other thing she’s not crazy about is my golf buddies parking their cart next to our rear fence on the golf course and then coming up my balcony stairs to my boudoir so they can have me pleasure their cock anyway they like it, blow their loads, and then leave like I’m running an upscale “in & out whorehouse” on my side of the house.
So, a couple weeks ago she lets me know that she is updating the guest bedroom and bathroom which is on my side of the house and adding a new door and entry into my office/boudoir for “more privacy.” I think the whole purpose is to isolate my sissy ass even more from her workers and the housekeeper, but as long as they don’t fuck with my French doors leading out to the gallery that my buddies use to come fuck me, then I’m okay with the whole process.
She may have reminded me on Monday that carpenters would be in the house taking measurements on Tuesday, but damned if I remembered. Or cared. I’m pretty ambivalent about what goes on around here. After breakfast I want to leave her to her business and go upstairs and shower, clean my ass, shave my cock and balls and upper torso, and dress in whatever makes me feel sexy that day. She accuses me of never paying attention to anything she says and something else but I don’t remember what it was.
Tuesday was a gorgeous day so I opened the French doors out to the gallery, and I could see a foursome in golf carts in the fairway adjacent to the house. If they could have seen me I was standing with my desk elevated, one laptop open to a Teams meeting I was barely listening to, with another laptop connected to a 30” monitor showing a clip of a beautiful big tit white woman with a black cock in her pussy while she’s sitting on a black cock in her ass and she’s humiliating her white husband to suck black cock. It was so fucking hot thinking of how my beautiful wife had been in so many of these settings and made me suck off the black men who had been fucking her. She and I would fuck all night after these sessions, neither of us getting enough big black cock.
I was standing in front of the monitors dressed in pink lace thigh highs with a pink G-string with a small glass butt plug in my ass that I couldn’t stop playing with and a very, very hard cock standing up outside my G-string, looking for attention. I pulled the butt plug out of my super clean asshole and put it in my mouth while I fingered my gaping asshole with two fingers and fucked my mouth with the butt plug.
I must have watched this clip for 15 minutes before the black cock in the wife’s ass shot his load in her ass and she got up, dripping his cum all over his cock and she made her cuckold husband get up and lick the cum off the black guy’s cock and made him suck it.
Dammit that scene was getting me so excited.
But something was a little off. I’m alone in this room 99% of my life and my wife never came here with me, but I couldn’t help but feel like I wasn’t alone. And I wasn’t.
I turned to my right and about ten feet behind me was a young Mexican man I recognized to be the son of the carpenter who was doing work for my wife in the house. He had come to measure my doorway to custom build a new door and there he was, staring at the monitor that I was watching stroking his hard cock as excited as I was watching the white husband lick off the cum and suck off this huge black cock. He had been watching the last five minutes, standing there ten feet behind me, with me being oblivious to his presence.
I panicked a bit as I removed my hand from my ass and took the butt plug from my mouth and laid it down on the desktop. I said excitedly, “Oh shit, I’m sorry. I didn’t know you were upstairs here with me.”
He was also startled that I caught him with me, but he recovered quickly. “It’s okay Mr. TD. I’m sorry but when I came in and I got excited when I saw you dressed in the stockings and Miss Eve naked in the movie like that, I couldn’t help but watch and then I was going to walk out but then you turned around and I was too excited.”
I didn’t expect him to say that. “You’re Jimmy, right?”
“Yes Sir, Jaime, but they call me Jimmy G.”
“Well Jimmy, I guess you watched long enough to realize that’s not Miss Eve in the movie?”
“Yes sir, all I saw at first was the big boobs and the blonde hair.”
“Yeah, the hair and the big tits would resemble my wife all right. Plus 15 years ago she and I would do just those things with other men in this house.”
All he could manage was a “Wow!”
I decided to take a chance with him. “Well Jimmy, if my pink stockings don’t turn you off, you’re welcome to watch the rest of the movie with me. Come here and we’ll watch the rest together.”
He didn’t hesitate. He moved up to the desk to get a closer look, never taking his hand off his cock.
Another move I felt was timely, “Jimmy, if it doesn’t bother you, I can help take care of that hard cock of yours. If it doesn’t offend you though, no pressure.”
He thought for a moment and I could tell I made him nervous. “Mr. TD, I watch the same kind of porn at home when I can. I’ve never done anything with another guy but I’ve been curious about it for a long time. I don’t know if I can though.”
“It’s okay Jimmy. You don’t have to do anything you’re uncomfortable with but let me stroke you so you can see how good it feels. If you don’t like it, I’ll stop, okay?”
He didn’t say anything but he took his hand from his cock and turned toward me, basically inviting me and making it easy to reach his cock. I placed my hand on his cock and gently caressed it and stroked it a couple times.
I reassured him. “You have a really nice cock Jimmy. I’m sure it feels good to have a stranger’s hand holding and stroking it, doesn’t it?”
“Yes sir, it feels awesome. It feels really good. How does it feel for you to hold it? Does it feel weird for you to hold another guy’s cock?”
“No, it doesn’t feel weird at all. From the first time, and you are a lot older than I was right now, it felt great. To have a cock in my hands or in my mouth or in my ass was the greatest feelings in the world for me… still is. Even a better feel for me than tits or pussy!”
Another “Wow.” And as he enjoyed my hand on his cock and the guy sucking cock in the video on my monitor, he couldn’t help but glance at my cock when he was not watching the movie or my hand moving on his cock.
Why not try him? “I see you looking at my cock Jimmy. Do you like it? Does it look good to you?”
“It’s huge Mr. TD. Your dick is twice as big as my little cock.”
“Nah, it’s not twice as big, just a little bigger. You’re welcome to pull my G-string down and feel it if you like, make me proud to say my cock was the first one you held in your hands.”
No hesitation, he pulled down the little thong and immediately grabbed my cock and began stroking it, no longer watching the video but watching in earnest as his hand moved up and down on my cock.
“Ooh fuck Jimmy, that feels so good. Your hand on my cock feels so fucking good, baby, just like you were made to stroke cock. Damn that feels good Jimmy. You’re a natural with cock baby!”
I could tell he liked the admiration. He never looked at my face. “Yeah, your cock feels good in my hand Mr. TD.”
“I’m glad you’re enjoying it, Jimmy. You’re like me a lot then. Hands feel good on your cock and cock feels good in your hands. If you want, you can play with my ass too. I’ve got a super clean and lubed up ass. I douched for about 20 minutes this morning before showering and ran a dildo in my ass in the shower to make sure I am squeaky clean… always have a clean ass.”
He was confused. “Douche?”
“Yeah, douche. I’ll explain it to you later. Go ahead and stick a finger or even two in my ass and see how that feels to you.”
Again, no hesitation, one, then two fingers in my ass and he begins fingering me while stroking my cock, and I don’t let up on making him feel good.”
“Oh yeah baby, your fingers in my ass feel so good while you stroke my cock. Oh, fuck yeah Jimmy, you’re a natural at this stuff. I’m beginning to believe you’re the expert at sucking cock and fucking and I’m the newbie. Oh, fuck yeah baby, that feels so fucking good. Fuck TD’s ass good baby, get all your hand all up in there.”
He liked this. He liked being egged on and being told what to do. I made the next move. “Go ahead and put my cock in your mouth Jimmy while I bend over and suck your cock and get it ready for my ass.”
Once again, he took my command and stuck my cock in his mouth and began bobbing on it like he had done it for ages. Another good use of porn. He had watched enough cocks being sucked by queers in porn vids that he had this down pat. I sucked on his cock just enough to get him wet and lubed up and then I stopped and told him, “I want you to fuck me, Jimmy. Just stay where you’re standing and let my cock and ass go and I’ll do all the work until you’re inside me.”
I turned my back to him and squatted with my ass against him as I guided his cock in my now well opened and well lubed ass. This kid is 5’7” max and it’s no minor “bend over” to get the ass of a 6’6” fag in the place it needs to be, but this ain’t my first rodeo and seconds later he’s pounding my ass like a seasoned activo joto in Tijuana.
“Oh, yeah, fuck me, Jimmy. Holy shit man you’re a natural for this. Fuck my big pussy and unload your nuts in me baby. Fuck me like that black guy is doing that white cuck on the monitor baby.”
That was too much for the poor young man. “I’m gonna cum TD.”
He dropped the “mister.” Now we’re fuck buddies and he doesn’t have to call me mister.
“Yeah baby. Unload your nuts in my big pussy. Yeah, fill me up Jimmy. Fill my big ass up baby!”
And he did. He could barely hold on to me because he was fucking me so hard, trying to get as deep and far up my man pussy as he could get. And he unloaded, and unloaded, and unloaded stream after stream of hot, juicy cum up my old queer sissy f.a.g.g.o.t ass. And as soon as my new former virgin top slipped out of my ass, I spun around in my crouch and sucked his cock until my lips had all of his pubes surrounded and he was too sensitive to stand any more. My baby was cleaned up and cleaned out.
He was finished and he was anxious to get the hell out of there before his dad came looking for him. I helped him with his measurements, and we exchanged cell numbers before he headed out and back downstairs.
I sat on the toilet and let his cum flow out of me freely and I texted him. “Jimmy, tell your Dad I want you to modify my cabinet door in my bathroom to match the new door and you need to come back around 2:00 PM to measure. And you can do it yourself, don’t need his help unless he wants some of this pussy too. And I need to cum on your cock next time too.”
About 10 minutes later, I got the response “See you at 2 TD and what about on my face and mouth instead.”
That’s my boy.
But the house was dated; it needed to be modernized, hence the great deal on the purchase price. So, every year my wife undertakes a modernization project for the spring and there are carpenters, electricians, plumbers, painters and the like all over the house taking care of her whims and wishes. Couple rooms at a time.
Well, so far my wife’s projects have not interfered with what I call “my side of the house.” Although we still love and cherish each other, we spend the day living fairly separate lives. We have three meals a day together and sleep together, but otherwise, I’m up in my “office/study/library/man-cave” on the computer and phone, managing our businesses, or I’m watching porn, or if I’m lucky, I’m sucking cock or getting fucked by a big, hard cock.
For those of you who know us, you know my wife and I have been active bisexual swingers since before we were married 50 years ago. We both loved pussy and cock until 2010 when menopause did more than just “pause” her sex life; it ended it. Well, her desires haven’t stopped me, although I haven’t had pussy since 2009, and that’s fine with me, and she’s good with that as well. What she’s not exactly crazy about is that I’m more of a sissy f.a.g.g.o.t than I’ve ever been and I spend the days in my upstairs office/boudoir if you would, dressed in the finest lace and fishnet and lingerie that can fit a 6’6”, 250 pound athletic, trim, and fit old queer.
The other thing she’s not crazy about is my golf buddies parking their cart next to our rear fence on the golf course and then coming up my balcony stairs to my boudoir so they can have me pleasure their cock anyway they like it, blow their loads, and then leave like I’m running an upscale “in & out whorehouse” on my side of the house.
So, a couple weeks ago she lets me know that she is updating the guest bedroom and bathroom which is on my side of the house and adding a new door and entry into my office/boudoir for “more privacy.” I think the whole purpose is to isolate my sissy ass even more from her workers and the housekeeper, but as long as they don’t fuck with my French doors leading out to the gallery that my buddies use to come fuck me, then I’m okay with the whole process.
She may have reminded me on Monday that carpenters would be in the house taking measurements on Tuesday, but damned if I remembered. Or cared. I’m pretty ambivalent about what goes on around here. After breakfast I want to leave her to her business and go upstairs and shower, clean my ass, shave my cock and balls and upper torso, and dress in whatever makes me feel sexy that day. She accuses me of never paying attention to anything she says and something else but I don’t remember what it was.
Tuesday was a gorgeous day so I opened the French doors out to the gallery, and I could see a foursome in golf carts in the fairway adjacent to the house. If they could have seen me I was standing with my desk elevated, one laptop open to a Teams meeting I was barely listening to, with another laptop connected to a 30” monitor showing a clip of a beautiful big tit white woman with a black cock in her pussy while she’s sitting on a black cock in her ass and she’s humiliating her white husband to suck black cock. It was so fucking hot thinking of how my beautiful wife had been in so many of these settings and made me suck off the black men who had been fucking her. She and I would fuck all night after these sessions, neither of us getting enough big black cock.
I was standing in front of the monitors dressed in pink lace thigh highs with a pink G-string with a small glass butt plug in my ass that I couldn’t stop playing with and a very, very hard cock standing up outside my G-string, looking for attention. I pulled the butt plug out of my super clean asshole and put it in my mouth while I fingered my gaping asshole with two fingers and fucked my mouth with the butt plug.
I must have watched this clip for 15 minutes before the black cock in the wife’s ass shot his load in her ass and she got up, dripping his cum all over his cock and she made her cuckold husband get up and lick the cum off the black guy’s cock and made him suck it.
Dammit that scene was getting me so excited.
But something was a little off. I’m alone in this room 99% of my life and my wife never came here with me, but I couldn’t help but feel like I wasn’t alone. And I wasn’t.
I turned to my right and about ten feet behind me was a young Mexican man I recognized to be the son of the carpenter who was doing work for my wife in the house. He had come to measure my doorway to custom build a new door and there he was, staring at the monitor that I was watching stroking his hard cock as excited as I was watching the white husband lick off the cum and suck off this huge black cock. He had been watching the last five minutes, standing there ten feet behind me, with me being oblivious to his presence.
I panicked a bit as I removed my hand from my ass and took the butt plug from my mouth and laid it down on the desktop. I said excitedly, “Oh shit, I’m sorry. I didn’t know you were upstairs here with me.”
He was also startled that I caught him with me, but he recovered quickly. “It’s okay Mr. TD. I’m sorry but when I came in and I got excited when I saw you dressed in the stockings and Miss Eve naked in the movie like that, I couldn’t help but watch and then I was going to walk out but then you turned around and I was too excited.”
I didn’t expect him to say that. “You’re Jimmy, right?”
“Yes Sir, Jaime, but they call me Jimmy G.”
“Well Jimmy, I guess you watched long enough to realize that’s not Miss Eve in the movie?”
“Yes sir, all I saw at first was the big boobs and the blonde hair.”
“Yeah, the hair and the big tits would resemble my wife all right. Plus 15 years ago she and I would do just those things with other men in this house.”
All he could manage was a “Wow!”
I decided to take a chance with him. “Well Jimmy, if my pink stockings don’t turn you off, you’re welcome to watch the rest of the movie with me. Come here and we’ll watch the rest together.”
He didn’t hesitate. He moved up to the desk to get a closer look, never taking his hand off his cock.
Another move I felt was timely, “Jimmy, if it doesn’t bother you, I can help take care of that hard cock of yours. If it doesn’t offend you though, no pressure.”
He thought for a moment and I could tell I made him nervous. “Mr. TD, I watch the same kind of porn at home when I can. I’ve never done anything with another guy but I’ve been curious about it for a long time. I don’t know if I can though.”
“It’s okay Jimmy. You don’t have to do anything you’re uncomfortable with but let me stroke you so you can see how good it feels. If you don’t like it, I’ll stop, okay?”
He didn’t say anything but he took his hand from his cock and turned toward me, basically inviting me and making it easy to reach his cock. I placed my hand on his cock and gently caressed it and stroked it a couple times.
I reassured him. “You have a really nice cock Jimmy. I’m sure it feels good to have a stranger’s hand holding and stroking it, doesn’t it?”
“Yes sir, it feels awesome. It feels really good. How does it feel for you to hold it? Does it feel weird for you to hold another guy’s cock?”
“No, it doesn’t feel weird at all. From the first time, and you are a lot older than I was right now, it felt great. To have a cock in my hands or in my mouth or in my ass was the greatest feelings in the world for me… still is. Even a better feel for me than tits or pussy!”
Another “Wow.” And as he enjoyed my hand on his cock and the guy sucking cock in the video on my monitor, he couldn’t help but glance at my cock when he was not watching the movie or my hand moving on his cock.
Why not try him? “I see you looking at my cock Jimmy. Do you like it? Does it look good to you?”
“It’s huge Mr. TD. Your dick is twice as big as my little cock.”
“Nah, it’s not twice as big, just a little bigger. You’re welcome to pull my G-string down and feel it if you like, make me proud to say my cock was the first one you held in your hands.”
No hesitation, he pulled down the little thong and immediately grabbed my cock and began stroking it, no longer watching the video but watching in earnest as his hand moved up and down on my cock.
“Ooh fuck Jimmy, that feels so good. Your hand on my cock feels so fucking good, baby, just like you were made to stroke cock. Damn that feels good Jimmy. You’re a natural with cock baby!”
I could tell he liked the admiration. He never looked at my face. “Yeah, your cock feels good in my hand Mr. TD.”
“I’m glad you’re enjoying it, Jimmy. You’re like me a lot then. Hands feel good on your cock and cock feels good in your hands. If you want, you can play with my ass too. I’ve got a super clean and lubed up ass. I douched for about 20 minutes this morning before showering and ran a dildo in my ass in the shower to make sure I am squeaky clean… always have a clean ass.”
He was confused. “Douche?”
“Yeah, douche. I’ll explain it to you later. Go ahead and stick a finger or even two in my ass and see how that feels to you.”
Again, no hesitation, one, then two fingers in my ass and he begins fingering me while stroking my cock, and I don’t let up on making him feel good.”
“Oh yeah baby, your fingers in my ass feel so good while you stroke my cock. Oh, fuck yeah Jimmy, you’re a natural at this stuff. I’m beginning to believe you’re the expert at sucking cock and fucking and I’m the newbie. Oh, fuck yeah baby, that feels so fucking good. Fuck TD’s ass good baby, get all your hand all up in there.”
He liked this. He liked being egged on and being told what to do. I made the next move. “Go ahead and put my cock in your mouth Jimmy while I bend over and suck your cock and get it ready for my ass.”
Once again, he took my command and stuck my cock in his mouth and began bobbing on it like he had done it for ages. Another good use of porn. He had watched enough cocks being sucked by queers in porn vids that he had this down pat. I sucked on his cock just enough to get him wet and lubed up and then I stopped and told him, “I want you to fuck me, Jimmy. Just stay where you’re standing and let my cock and ass go and I’ll do all the work until you’re inside me.”
I turned my back to him and squatted with my ass against him as I guided his cock in my now well opened and well lubed ass. This kid is 5’7” max and it’s no minor “bend over” to get the ass of a 6’6” fag in the place it needs to be, but this ain’t my first rodeo and seconds later he’s pounding my ass like a seasoned activo joto in Tijuana.
“Oh, yeah, fuck me, Jimmy. Holy shit man you’re a natural for this. Fuck my big pussy and unload your nuts in me baby. Fuck me like that black guy is doing that white cuck on the monitor baby.”
That was too much for the poor young man. “I’m gonna cum TD.”
He dropped the “mister.” Now we’re fuck buddies and he doesn’t have to call me mister.
“Yeah baby. Unload your nuts in my big pussy. Yeah, fill me up Jimmy. Fill my big ass up baby!”
And he did. He could barely hold on to me because he was fucking me so hard, trying to get as deep and far up my man pussy as he could get. And he unloaded, and unloaded, and unloaded stream after stream of hot, juicy cum up my old queer sissy f.a.g.g.o.t ass. And as soon as my new former virgin top slipped out of my ass, I spun around in my crouch and sucked his cock until my lips had all of his pubes surrounded and he was too sensitive to stand any more. My baby was cleaned up and cleaned out.
He was finished and he was anxious to get the hell out of there before his dad came looking for him. I helped him with his measurements, and we exchanged cell numbers before he headed out and back downstairs.
I sat on the toilet and let his cum flow out of me freely and I texted him. “Jimmy, tell your Dad I want you to modify my cabinet door in my bathroom to match the new door and you need to come back around 2:00 PM to measure. And you can do it yourself, don’t need his help unless he wants some of this pussy too. And I need to cum on your cock next time too.”
About 10 minutes later, I got the response “See you at 2 TD and what about on my face and mouth instead.”
That’s my boy.
1ヶ月前
