Turning a straight guy stories?

[drobert44]

I don't believe so. I think true sissies genuinely want to adopt a feminine guise, do the makeup, hair, clothes and voice as well as the lingerie.

Although I wear lingerie for masturbating and sex I wouldn't ever call myself a sissy. I'm just a bi guy with a fetish for panties and stockings.

Sissies wanna be femme, and I treat them like girls. Their cock is a clit, etc.

 

[Oyster69]

I’m a gay guy who has a real fetish for jacking off straight men. I subscribe to a UK adult site and included in my Profile description I state that I’m seeking straight (particularly married) guys who would enjoy receiving an expert slow, edging handjob while watching porn.

Needless to say, I have enjoyed pleasuring a large number of gorgeous straight and very hard cocks over the years. I remember one particular chap, largely because he was the youngest respondent to date. He was a very cute 18 year old who told me he was straight and very nervous as he’d never done anything like this before.

I assured him that if at any point he felt uncomfortable I would halt the proceedings and he could leave without any hard feelings. He sat next to me on my sofa fully dressed (as I was) and I put some straight porn on. He was visibly shaking as the video started, which prompted me to ask him: “Would you rather I sat further away?” He insisted he was ok with the situation as it was. As the video got a bit hotter and some serious action on the screen developed, I glanced down at his crotch which I noticed was beginning to show promise. Ironically, the video depicted a sexy milf seducing a young man.

When my young man stretched his legs out in front of him and adjusted his enlarging bulge I took it at as my cue to take the initiative. I placed my hand on his thigh which made him start. “You ok?” I asked. “Yes,” he replied. I squeezed his thigh gently, then my wandering fingers made their way to their goal.

His whole body twitched when I cupped the clothed bulge in my hand.

“You ok?” I asked again. “Yes,” he croaked. I unbuckled his trouser belt and unzipped his fly. My hand fished inside and found his now fully erect cock sheathed inside his underpants. As I stroked the outside of his his briefs and felt his weapon twitch, I whispered: “Do you want me to carry on?” He nodded and muttered “Please.”

I asked him to raise his buttocks up so I could slide his trousers and underpants down. His young, lovely erection flipped into the open. I remember his cock not being over large, but, my God, was it rock hard.
As I gently grasped it in my full fist, my other hand fondling his spunk-filled balls, I was aware that mine were the first male hands other than his own to be touching his genitals and his reaction showed that he found it hugely gratifying.

When I give a guy a handjob I like to employ different hand techniques and speeds and I treated my young virgin to each one. I think he was equally turned on watching my hands working their magic on his prick and balls as the action on the screen. His pre-cum was oozing quite vociferously now and I sensed he wasn’t going to last much longer.

I lowered my head and took his uncut cock in my mouth, tasting his sweet pre-cum as I licked under his foreskin round his nob-end. This really did get him going and he couldn’t resist an: “Oh, fuck!”
“Are you getting close?”
“Yes” he replied.
“Would you like to cum on my face?”
“Yes” he replied again.
I laid my cheek on his navel and started sucking his cock again, this gorgeous organ merely a few inches from my face. My other hand, reached down to manipulate his balls as I brought him off. It didn’t take long.

His belly tightened and breathing became faster as I stroked and sucked faster. Rather than warning me with words, his grunts and gasps indicated his impending ejaculation. I felt the first jet hit the back of my throat, then as I withdrew my mouth, my wanking hand milked several more ropes of his thick cum over my face.

After wiping both of us down with a towel, he dressed quickly. I had the feeling he didn’t want to hang about for long.

“I hope you enjoyed that.” I said.
“Yeah, it was great, thanks.” he replied.
“You’ve got my number,” I said. “If you want to come back for some more, you’re very welcome.”

As I showed him out of my door, I had a feeling I wouldn’t see him again. Sadly, I was right.

So, perhaps I didn’t turn this straight young man, but I’m sure as a “curious”experiment, he found it enjoyable, if not habit-forming.

That is one of my favorite ways of getting a blow job, it leaves hands free to pinch nipples, play with your cock and grab your ass.

 

[Flyover3]

Sissies wanna be femme, and I treat them like girls. Their cock is a clit, etc.

Ya, I want to be all woman, dressed in sexy lingerie and on my knees, sucking cock before
being on my back. A man's gorgeous cock inside me, while we kiss.

 

[Easyvirtue]

Being a crossdresser all my life I still never had seen myself as bi or gay or whatever. I loved being dressed for my girlfriends or when I was alone. I knew I was hyper sexual and loved all things sex, ALL THINGS, but still never thought or dreamed I’d have those tendencies. Wasn’t till one friend in our circle came out. From that point he seemed to look at me different and maybe because I found myself finally wondering..hmmmmmm.
So obviously one night that all changed and it was me who took the chance and made a move. We still are friends to this day but I’m now married and so is he, but that lit a fire deep down inside, and I do fantasize and wonder about being with another man again.

 

[tristantrotsky]

I don't believe so. I think true sissies genuinely want to adopt a feminine guise, do the makeup, hair, clothes and voice as well as the lingerie.

Although I wear lingerie for masturbating and sex I wouldn't ever call myself a sissy. I'm just a bi guy with a fetish for panties and stockings.

The true test is when you're dressed and you meet a guy in a bar, and he takes you out into his car where you get his cock out and suck him off. Then you fix your makeup and return to the bar, leaving him there still thinking he's been sucked-off by a woman!

 

[Sunnyade]

Not so much turning him gay as giving him the opportunity to indulge beyond cocksucking. I bottomed for him first knowing that I'd get to fuck him further down the road.

 

[herrdrier]

I drove limo part time in Houston many years ago. Picked up a group of guys from a nice hotel and they were planning on a night out on the town.
A LOT of white powder was consumed and they were getting pretty rowdy and loud. I put up the partition and before too long there was a knock on the divider. They wanted to stop at a liquor store and asked me to go in to pick up the beverages. I came back to the car, put down the divider to hand it over and was shocked by what I saw. 5 naked guys sucking, rimming, and screwing. I wasn't sure what to do so I pulled into a mall parking lot away from the road and let them enjoy there time. Curiosity got the better of me and I slowly put the divider down a little at a time so I could watch. Married guy and had never seen anything like this.
I found that I was getting aroused and very hard. I couldn't help it and just pulled out my raging erection and started stroking myself to the action. One of the guys ended up getting on his knees facing the front as he was getting drilled and saw me watching. He motioned for me to turn around to face him. I was conflicted for a while but when another took his turn behind him I was mesmerized.

I turned around, and he reached over and started stroking me. The first time any male hand other than my own stroked me.
Eventually after being invited to join them in the back again and again, and promised the best blow job of my life my hormones got the better of me. I put up the divider, climbed into the back and locked the doors.

It felt like being attacked by an octopus, my clothes were promptly removed and the assault began. Hands all over me, mouth on my shaft, tongue on my balls, nipples getting sucked. Sensory overload. Things progressed to the point where I went from one end of a spit roast to the other.

I dropped them off at their hotel as the sun was coming up, physically drained with the biggest tip I ever received.

I think about that a lot these days and fantasize about what could have been. In my later years I tried to live out my fantasies from this night.

 

[stargame]

I drove limo part time in Houston many years ago. Picked up a group of guys from a nice hotel and they were planning on a night out on the town.
A LOT of white powder was consumed and they were getting pretty rowdy and loud. I put up the partition and before too long there was a knock on the divider. They wanted to stop at a liquor store and asked me to go in to pick up the beverages. I came back to the car, put down the divider to hand it over and was shocked by what I saw. 5 naked guys sucking, rimming, and screwing. I wasn't sure what to do so I pulled into a mall parking lot away from the road and let them enjoy there time. Curiosity got the better of me and I slowly put the divider down a little at a time so I could watch. Married guy and had never seen anything like this.
I found that I was getting aroused and very hard. I couldn't help it and just pulled out my raging erection and started stroking myself to the action. One of the guys ended up getting on his knees facing the front as he was getting drilled and saw me watching. He motioned for me to turn around to face him. I was conflicted for a while but when another took his turn behind him I was mesmerized.

I turned around, and he reached over and started stroking me. The first time any male hand other than my own stroked me.
Eventually after being invited to join them in the back again and again, and promised the best blow job of my life my hormones got the better of me. I put up the divider, climbed into the back and locked the doors.

It felt like being attacked by an octopus, my clothes were promptly removed and the assault began. Hands all over me, mouth on my shaft, tongue on my balls, nipples getting sucked. Sensory overload. Things progressed to the point where I went from one end of a spit roast to the other.

I dropped them off at their hotel as the sun was coming up, physically drained with the biggest tip I ever received.

I think about that a lot these days and fantasize about what could have been. In my later years I tried to live out my fantasies from this night.

I am now living vicariously through you

 

[WerdNerd]

I drove limo part time in Houston many years ago. Picked up a group of guys from a nice hotel and they were planning on a night out on the town.
A LOT of white powder was consumed and they were getting pretty rowdy and loud. I put up the partition and before too long there was a knock on the divider. They wanted to stop at a liquor store and asked me to go in to pick up the beverages. I came back to the car, put down the divider to hand it over and was shocked by what I saw. 5 naked guys sucking, rimming, and screwing. I wasn't sure what to do so I pulled into a mall parking lot away from the road and let them enjoy there time. Curiosity got the better of me and I slowly put the divider down a little at a time so I could watch. Married guy and had never seen anything like this.
I found that I was getting aroused and very hard. I couldn't help it and just pulled out my raging erection and started stroking myself to the action. One of the guys ended up getting on his knees facing the front as he was getting drilled and saw me watching. He motioned for me to turn around to face him. I was conflicted for a while but when another took his turn behind him I was mesmerized.

I turned around, and he reached over and started stroking me. The first time any male hand other than my own stroked me.
Eventually after being invited to join them in the back again and again, and promised the best blow job of my life my hormones got the better of me. I put up the divider, climbed into the back and locked the doors.

It felt like being attacked by an octopus, my clothes were promptly removed and the assault began. Hands all over me, mouth on my shaft, tongue on my balls, nipples getting sucked. Sensory overload. Things progressed to the point where I went from one end of a spit roast to the other.

I dropped them off at their hotel as the sun was coming up, physically drained with the biggest tip I ever received.

I think about that a lot these days and fantasize about what could have been. In my later years I tried to live out my fantasies from this night.

You're making me want to give you a big tip...

 

[oldsurreyman]

Something like this?

you look amazing!

 

[Randomguy126]

Something like this?

Very cute

 

[JoeSmith2022]

I would role-play this for the right guy.

 

[Phatfeet]

Since the only men I have been with have been gay and not bisexual men, nor even married men, I have never had the pleasure of giving a blowjob to a guy who has never had a blowjob given to them in a male-male way before. Not that I feel “used” in any way as the men I have given them too seem to be been pleased with what I did for them and seemed genuine in thanking me. But I think it would be interesting to see a first-timers reaction to one I have given him.

I would only have one question after I was done: would you like me to do it again sometime?

I think the answer to that would be empowering or demoralizing depending upon his answer.

 

[Bisexguy70]

Since the only men I have been with have been gay and not bisexual men, nor even married men, I have never had the pleasure of giving a blowjob to a guy who has never had a blowjob given to them in a male-male way before. Not that I feel “used” in any way as the men I have given them too seem to be been pleased with what I did for them and seemed genuine in thanking me. But I think it would be interesting to see a first-timers reaction to one I have given him.

I would only have one question after I was done: would you like me to do it again sometime?

I think the answer to that would be empowering or demoralizing depending upon his answer.

I think id love to have you suck my dick. If you wanted me to id act as if id never had one before i would. I know youd do a wonderful job because I sense you have the strong desire to be good at it. Simply by the question “would you like me to do it again”.
You want him to say yes therefore your going to work very hard at using your tongue and mouth to please.

 

[Replicant2018]

Since the only men I have been with have been gay and not bisexual men, nor even married men, I have never had the pleasure of giving a blowjob to a guy who has never had a blowjob given to them in a male-male way before. Not that I feel “used” in any way as the men I have given them too seem to be been pleased with what I did for them and seemed genuine in thanking me. But I think it would be interesting to see a first-timers reaction to one I have given him.

I would only have one question after I was done: would you like me to do it again sometime?

I think the answer to that would be empowering or demoralizing depending upon his answer.

Wish my spouse felt the same way.

 

[SPARTAN047]

Yes, totally, I've always wanted to be treated like a sweet feminine bottom and a slut, but a loved and cherished one.

 

[Jeph77]

Since the only men I have been with have been gay and not bisexual men, nor even married men, I have never had the pleasure of giving a blowjob to a guy who has never had a blowjob given to them in a male-male way before. Not that I feel “used” in any way as the men I have given them too seem to be been pleased with what I did for them and seemed genuine in thanking me. But I think it would be interesting to see a first-timers reaction to one I have given him.

I would only have one question after I was done: would you like me to do it again sometime?

I think the answer to that would be empowering or demoralizing depending upon his answer.

Better not to ask then, but when he's texting you a week later, you have your answer. Let him think he's the one who's obsessed. That's hot.

 

[SPARTAN047]

I only want to be the bottom lover - generally. If I'm allowed to fuck my Domme while they're still in charge or they bring another submissive sissy Slut for me to fuck, it's okay. Assuming we're fucking others or having group sex, but I don't want that to be the priority.

 

[Beachguy23]

I find the thought of turning a straight guy extremely arousing , I assume he would be a married man that gets little or none at home , or perhaps has reached a stage in his life were he has thought of acting on fantasies. Without a doubt I’m sure I would be able to make him tremble in ways he only just barely remembers from early days of his relationship. Not bragging but I’m sure I can suck the life out of him. Plus I just think it would be fun

 

[Replicant2018]

I find the thought of turning a straight guy extremely arousing , I assume he would be a married man that gets little or none at home , or perhaps has reached a stage in his life were he has thought of acting on fantasies. Without a doubt I’m sure I would be able to make him tremble in ways he only just barely remembers from early days of his relationship. Not bragging but I’m sure I can suck the life out of him. Plus I just think it would be fun

Certainly a fantasy of mine.

 

[SPARTAN047]

I find the thought of turning a straight guy extremely arousing , I assume he would be a married man that gets little or none at home , or perhaps has reached a stage in his life were he has thought of acting on fantasies. Without a doubt I’m sure I would be able to make him tremble in ways he only just barely remembers from early days of his relationship. Not bragging but I’m sure I can suck the life out of him. Plus I just think it would be fun

Forbidden fruit.

 

[Oscarmeyer50]

Something like this?

Wow!!! You are sexy. Love that I can see the outline of your cock. I would be defenseless against you. I think you could turn me from bi-curious to cocksucker pretty quickly.

 

[Zippy100]

I know what you mean about changing trajectories, although mine took a long time to change. I've been sexually straight most of my life, married, kids etc, but started chatting online and exploring that way a few years ago and finally, this year got to the nitty-gritty of actually meeting a couple of guys.

Hadn't been completely sure of how I'd go, but it felt natural once we got out of our male clothes and I was confronted with another man's excited penis. I was like, sucking and riding cock is SO good, why didn't I do this sooner?

Does your wife know

 

[Zippy100]

Perhaps I'm naive, but it never occurred to me that "turning" someone involved forcing myself on a man. I just want to make him so hot that he wants me to be his first. Really good for my ego.

Not that I've ever done it. Hoping to change that soon.

I've rubbed my cock on a straight guy's ass in a club. He loved it

 

[Zippy100]

Ya, I want to be all woman, dressed in sexy lingerie and on my knees, sucking cock before
being on my back. A man's gorgeous cock inside me, while we kiss.

I have dressed up in the past.