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Being a mans first time

Sissy_LoriLux said:
Since a lot of the PMs I get are guys curious about sissies and never actually played I've been sharing stories and they're kind of hot so if you were ever someone's first time I'd love to also hear some stories.

One experience that's stuck with me was an older man. I was 22 and he was 65. His wife had passed away a few years prior and he was curious to try new things. We began chatting online and he wanted to visit. Soon the date was arranged. It was a Saturday night.

I wore a red cock tail dress with lace lingerie underneath. I greeted him at the door. He brought some gin and seltzer over. We both sat on the couch and had a few drinks while chatting. He was very shy but he was definitely checking me out the more he drank.

I slowly slid closer to him as we chatted. He began feeling my upper legs. He had big rough hands. I began to rub his crotch over his jeans. He was hard. I undid his belt and he shimmied out of his pants. I got down on the floor and began slowly kissing and licking his cock while he sat on the couch. Soon the entire thing was in my mouth. I could feel he was really enjoying himself.

I stood up and turned around. I bent over and pulled my dress up revealing my sissy pussy and asked him "is there anything else you want to try". He stood up and put me on the couch doggy style. He slapped my ass and pushed against my hole. I had toyed a bit getting ready for him so his cock covered with my spit entered nicely. He stroked in and out of me for only about 30 seconds and came right away. He pulled out and spread my cheeks and looked at my hole. "Holy fuck I wasn't expecting that" he said.

He was a little apologetic about his stamina and speed but I didn't mind it was really hot knowing I was his first and he loved it. Soon he started visiting any time he could.
Click to expand...
This sounds incredible. I would love to be a first time for someone one day. Of course I have to get my first time out of the way! Not sure I would look as good in a cocktail dress though.
 
Sissy_LoriLux said:
That's a very sexy story. I had an organic hook up with a straight black guy once.

Me and some other girlfriends were out at a club. He kept dancing with me and bought me a couple drinks.

When we left he came outside behind us. He asked where we were going. We told him home. He asked if I wanted to go with him instead. I told him I wasn't actually a woman. He looked around the street and shrugged and said he was curious. I agreed to go with him.

We walked to his car together. It was in an underground parking lot. We both got in the car but he didn't start it. He grabbed my face and started making out with me. He told me "you kiss like a girl, but do you suck like one" and pulled his pants down.

I bent over and began sucking his cock. It was pretty big and I did my best to really please him. After a couple of minutes he stopped me. "I'm gonna bust in your mouth if you keep doing it like that" he said. He pulled his pants back up and started to drive.

He asked about sex while driving. He told me he just wanted ass and nothing to do with my cock. I told him that was okay. I told him we should get lube. He stopped at a gas station and got condoms and lube.

When we got to his place he brought me immediately to his bedroom. I think he had room mates that were asleep. I got on the bed and got into a doggy style position because he said in the car that's how he wanted it. I pulled my panties down just enough to show my hole and pulled my dress up. He put on a condom and lubed up his cock. He struggled a bit getting it in. I helped guide it in and soon he was deep in me. He fucked me hard.

He bottomed out in me, *most bitches can't take it this deep" he whispered. Then I felt the unmistakable feeling of a hard cock pulsating out cum. He slapped my ass and pulled out. We traded numbers. I left and got an Uber home.

He was left confused sometimes drunk he would try to hook up with me, but also tell me he was straight and not gay sober and it was a one time thing. Lol
Click to expand...
Sad that it was a one time thing.
 
I was at a company party sitting next to an older man whose leg kept bumping mine. I quit moving mine away and soon we were just resting against one another. His hand rested on my leg and then my crotch. As long as I didn't oppose, he got bolder. I excused myself and went to the bathroom to beat off. One minute later he was behind me and asked if I wanted to visit his hotel room. Once we got there he unzipped my pants and pulled out my cock. I was really surprised when he said he'd never done it before. What? He was at least 45 - twice my age. Anyway, after a few minutes of his handjob I asked if he wanted to have sex. He agreed but needed lube. We settled for cheap hotel lotion. It worked - more or less. He got on the bed - hands and knees - while I entered his hole. He made a lot of noise but it was nice once we got up to speed.
 
Ciceri said:
I was at a company party sitting next to an older man whose leg kept bumping mine. I quit moving mine away and soon we were just resting against one another. His hand rested on my leg and then my crotch. As long as I didn't oppose, he got bolder. I excused myself and went to the bathroom to beat off. One minute later he was behind me and asked if I wanted to visit his hotel room. Once we got there he unzipped my pants and pulled out my cock. I was really surprised when he said he'd never done it before. What? He was at least 45 - twice my age. Anyway, after a few minutes of his handjob I asked if he wanted to have sex. He agreed but needed lube. We settled for cheap hotel lotion. It worked - more or less. He got on the bed - hands and knees - while I entered his hole. He made a lot of noise but it was nice once we got up to speed.
Click to expand...
Wow, that was brave of him. Something must have given him confidence that you were so inclined. I'll remember this if anyone ever rubs their leg against mine.
 
His bumping under the table was continuous. He wasn't subtle at all. He said he'd had his eye on me at work. I'd never really noticed him before that night
 
Ciceri said:
His bumping under the table was continuous. He wasn't subtle at all. He said he'd had his eye on me at work. I'd never really noticed him before that night
Click to expand...
I sounds to me you may have had same sex relations before and maybe he knew it?
 
Years ago, I used to work part time as a front desk associate at a very popular business hotel. My colleague was a beautiful woman in her early thirties. Lots of men used to hit on her regularly, usually in their late thirties to even in their sixties. If the man was well groomed, she would accept their advances and go to their rooms. She would accept gifts and money, but not always. Sometimes she would share some details of their sex, or she would ask the guy to take their pictures and videos and she would show it to me.
https://cdn03.imaglr.com/storage/uploads/4445/2026/08/w1B8fsm4O6Ve9KB5EK10WuX813EeLRfEmIyR53Rb.jpg
https://cdn03.imaglr.com/storage/uploads/155065/2026/08/j0aYAzH8cRKJr9piNGSUDlPmGcMSiE2ktUAdtnNM.gif

One night, she went up with one of the guests to his room. A few hours later they came down and walked up to the front desk. She introduced him to me and we chatted about nothing. Then he went out to meet some friends and my colleague joined me behind the desk.
"Looks like you both had a good time?" I quipped. "Yes. He's great in bed" she said.
"In fact, he wanted to know if you would like to join us next time" she giggled.
"What do you mean?" I asked.
"I told him about your photograph" she laughed.
"What!!" I said.. I was embarrassed. I knew what she was referring to.
In college, I had a friend who was studying some courses in acting and theatre. He had a big kit of attires and makeup. One night, I tried on some makeup and wig and took some photographs. One of them I took in the nude.
https://cdn03.imaglr.com/storage/uploads/134457/2026/07/7QJC9cWocNltWGqAY207iLq9nH9sUQqfgd7yVYCA.jpg
I also fooled around with him that night... https://cdn03.imaglr.com/storage/uploads/73678/2025/12/T2r4i7GQgfQ3rp2uBAUcMYL4YD4hJYwKF6zirqEd.gif. But we didn't go beyond some hand jobs.
Since then I harbored a thought of being with a man, but never had the courage to go forward with it.

"So, what do you think?" she asked. "This is a good chance to try out your wish. He's a good man too"
"I am not sure" I replied, feeling a bit embarrassed.
A large group of guests walked in and we got busy with their check-in process. It took almost an hour. We then finished our shifts and went to the kitchen to grab a bite.

While at it, she got a call. Her guest was back. She said she would join him within the hour and bring me along. I looked up at her surprised.. but she winked at me. "He's here with me. We'll come together" she told him.

"Don't worry. it will be fun' she told me. We chatted for a while over coffee. Then we changed to our regular clothes and she led me to his room.

https://cdn03.imaglr.com/storage/uploads/45553/2025/10/6QcnFv4JCAi88V7BVGA1jPrTGp6K04OONDGKrKYO.jpg
I soon got down to work.
https://cdn03.imaglr.com/storage/uploads/1663/2025/01/u3c2p6I5Urcj9nsEln5xOm7SLONMRPBoanlYnwwx.gif
I worked on his cock for ten minutes while she made him eat her out. In the end he shot his load down my throat.
https://cdn03.imaglr.com/storage/uploads/5856/2025/08/sKw5PFsYNoZJGhvvOUurvM4QTzkC4nQ7sbt9DG6S.mp4

And that was the beginning of my bisexual adventures.
 
aquam34 said:
Years ago, I used to work part time as a front desk associate at a very popular business hotel. My colleague was a beautiful woman in her early thirties. Lots of men used to hit on her regularly, usually in their late thirties to even in their sixties. If the man was well groomed, she would accept their advances and go to their rooms. She would accept gifts and money, but not always. Sometimes she would share some details of their sex, or she would ask the guy to take their pictures and videos and she would show it to me.
https://cdn03.imaglr.com/storage/uploads/4445/2026/08/w1B8fsm4O6Ve9KB5EK10WuX813EeLRfEmIyR53Rb.jpg
https://cdn03.imaglr.com/storage/uploads/155065/2026/08/j0aYAzH8cRKJr9piNGSUDlPmGcMSiE2ktUAdtnNM.gif

One night, she went up with one of the guests to his room. A few hours later they came down and walked up to the front desk. She introduced him to me and we chatted about nothing. Then he went out to meet some friends and my colleague joined me behind the desk.
"Looks like you both had a good time?" I quipped. "Yes. He's great in bed" she said.
"In fact, he wanted to know if you would like to join us next time" she giggled.
"What do you mean?" I asked.
"I told him about your photograph" she laughed.
"What!!" I said.. I was embarrassed. I knew what she was referring to.
In college, I had a friend who was studying some courses in acting and theatre. He had a big kit of attires and makeup. One night, I tried on some makeup and wig and took some photographs. One of them I took in the nude.
https://cdn03.imaglr.com/storage/uploads/134457/2026/07/7QJC9cWocNltWGqAY207iLq9nH9sUQqfgd7yVYCA.jpg
I also fooled around with him that night... https://cdn03.imaglr.com/storage/uploads/73678/2025/12/T2r4i7GQgfQ3rp2uBAUcMYL4YD4hJYwKF6zirqEd.gif. But we didn't go beyond some hand jobs.
Since then I harbored a thought of being with a man, but never had the courage to go forward with it.

"So, what do you think?" she asked. "This is a good chance to try out your wish. He's a good man too"
"I am not sure" I replied, feeling a bit embarrassed.
A large group of guests walked in and we got busy with their check-in process. It took almost an hour. We then finished our shifts and went to the kitchen to grab a bite.

While at it, she got a call. Her guest was back. She said she would join him within the hour and bring me along. I looked up at her surprised.. but she winked at me. "He's here with me. We'll come together" she told him.

"Don't worry. it will be fun' she told me. We chatted for a while over coffee. Then we changed to our regular clothes and she led me to his room.

https://cdn03.imaglr.com/storage/uploads/45553/2025/10/6QcnFv4JCAi88V7BVGA1jPrTGp6K04OONDGKrKYO.jpg
I soon got down to work.
https://cdn03.imaglr.com/storage/uploads/1663/2025/01/u3c2p6I5Urcj9nsEln5xOm7SLONMRPBoanlYnwwx.gif
I worked on his cock for ten minutes while she made him eat her out. In the end he shot his load down my throat.
https://cdn03.imaglr.com/storage/uploads/5856/2025/08/sKw5PFsYNoZJGhvvOUurvM4QTzkC4nQ7sbt9DG6S.mp4

And that was the beginning of my bisexual adventures.
Click to expand...
I love your style ❤️
 
aquam34 said:
Years ago, I used to work part time as a front desk associate at a very popular business hotel. My colleague was a beautiful woman in her early thirties. Lots of men used to hit on her regularly, usually in their late thirties to even in their sixties. If the man was well groomed, she would accept their advances and go to their rooms. She would accept gifts and money, but not always. Sometimes she would share some details of their sex, or she would ask the guy to take their pictures and videos and she would show it to me.
https://cdn03.imaglr.com/storage/uploads/4445/2026/08/w1B8fsm4O6Ve9KB5EK10WuX813EeLRfEmIyR53Rb.jpg
https://cdn03.imaglr.com/storage/uploads/155065/2026/08/j0aYAzH8cRKJr9piNGSUDlPmGcMSiE2ktUAdtnNM.gif

One night, she went up with one of the guests to his room. A few hours later they came down and walked up to the front desk. She introduced him to me and we chatted about nothing. Then he went out to meet some friends and my colleague joined me behind the desk.
"Looks like you both had a good time?" I quipped. "Yes. He's great in bed" she said.
"In fact, he wanted to know if you would like to join us next time" she giggled.
"What do you mean?" I asked.
"I told him about your photograph" she laughed.
"What!!" I said.. I was embarrassed. I knew what she was referring to.
In college, I had a friend who was studying some courses in acting and theatre. He had a big kit of attires and makeup. One night, I tried on some makeup and wig and took some photographs. One of them I took in the nude.
https://cdn03.imaglr.com/storage/uploads/134457/2026/07/7QJC9cWocNltWGqAY207iLq9nH9sUQqfgd7yVYCA.jpg
I also fooled around with him that night... https://cdn03.imaglr.com/storage/uploads/73678/2025/12/T2r4i7GQgfQ3rp2uBAUcMYL4YD4hJYwKF6zirqEd.gif. But we didn't go beyond some hand jobs.
Since then I harbored a thought of being with a man, but never had the courage to go forward with it.

"So, what do you think?" she asked. "This is a good chance to try out your wish. He's a good man too"
"I am not sure" I replied, feeling a bit embarrassed.
A large group of guests walked in and we got busy with their check-in process. It took almost an hour. We then finished our shifts and went to the kitchen to grab a bite.

While at it, she got a call. Her guest was back. She said she would join him within the hour and bring me along. I looked up at her surprised.. but she winked at me. "He's here with me. We'll come together" she told him.

"Don't worry. it will be fun' she told me. We chatted for a while over coffee. Then we changed to our regular clothes and she led me to his room.

https://cdn03.imaglr.com/storage/uploads/45553/2025/10/6QcnFv4JCAi88V7BVGA1jPrTGp6K04OONDGKrKYO.jpg
I soon got down to work.
https://cdn03.imaglr.com/storage/uploads/1663/2025/01/u3c2p6I5Urcj9nsEln5xOm7SLONMRPBoanlYnwwx.gif
I worked on his cock for ten minutes while she made him eat her out. In the end he shot his load down my throat.
https://cdn03.imaglr.com/storage/uploads/5856/2025/08/sKw5PFsYNoZJGhvvOUurvM4QTzkC4nQ7sbt9DG6S.mp4

And that was the beginning of my bisexual adventures.
Click to expand...
Excellent story and I love the way you incorporated in the clips.
 
Sissy_LoriLux said:
Since a lot of the PMs I get are guys curious about sissies and never actually played I've been sharing stories and they're kind of hot so if you were ever someone's first time I'd love to also hear some stories.

One experience that's stuck with me was an older man. I was 22 and he was 65. His wife had passed away a few years prior and he was curious to try new things. We began chatting online and he wanted to visit. Soon the date was arranged. It was a Saturday night.

I wore a red cock tail dress with lace lingerie underneath. I greeted him at the door. He brought some gin and seltzer over. We both sat on the couch and had a few drinks while chatting. He was very shy but he was definitely checking me out the more he drank.

I slowly slid closer to him as we chatted. He began feeling my upper legs. He had big rough hands. I began to rub his crotch over his jeans. He was hard. I undid his belt and he shimmied out of his pants. I got down on the floor and began slowly kissing and licking his cock while he sat on the couch. Soon the entire thing was in my mouth. I could feel he was really enjoying himself.

I stood up and turned around. I bent over and pulled my dress up revealing my sissy pussy and asked him "is there anything else you want to try". He stood up and put me on the couch doggy style. He slapped my ass and pushed against my hole. I had toyed a bit getting ready for him so his cock covered with my spit entered nicely. He stroked in and out of me for only about 30 seconds and came right away. He pulled out and spread my cheeks and looked at my hole. "Holy fuck I wasn't expecting that" he said.

He was a little apologetic about his stamina and speed but I didn't mind it was really hot knowing I was his first and he loved it. Soon he started visiting any time he could.
Click to expand...

Hi Sis:
So artfully written are your 6 paragraphs. Clear despite lots of new info. Emotions of nervousness, excitement and decency communicated. Wonderful, thank for the vignette
 
I have been the first oral sex partner for at least five men. And once agreed to a golden shower experiment with a really handsome lover, it was the first and last for me, it wasn't bad but I never felt any excitement after.
 
It's an incredible experience being a man's 'first time', especially a str8 or Bi curious guy, it's like introducing him to a whole new world of sexual exploration that he has just discovered and enjoyed....

I remember one such moment happened after I'd started living as a woman full time, I'd been xdressing for a decade previously and on a hormone treatment for around half of that time.

I was due a digital rectal examination on my prostate, when I went in to my regular doctor I was greeted by a locum doctor, a lovely man around half my age. He seemed mesmerised by my deep, plump cleavage and long blonde hair cascading over them, he looked a bit flummoxed.

'There must be some clerical mix up, it says you're here for a prostate examination?', he looked ever so confused, bless him, he obviously hadn't read my medical notes.

'That's right.' I confirmed, crossing and uncrossing my long slender smooth legs, in my rather naughty short skirt, looking at him rather seductively, he was a dish.

Then I think the penny dropped, he must have read the notes about hormone treatment and gender etc, 'ah, ok, right, I see now.....', he stumbled his words quite embarrassingly, 'sorry, I do apologise, I didn't mean to offended you, err Felicity'.

'You can call me Fliss...', I smiled and winked at him.

'Right we'll get on with the examination, could you slip your knickers off behind the screen please and just lay on the bed on your side, I'll just get a nurse to assist'

I quickly added, 'I'm not wearing any...', again he was looking very flustered and stared at my peachy ass in my figure hugging short skirt as I slipped behind the curtain, laying on the examination table, hitching it up.

I waited until the nurse came and joined him, nervously he slipped on a latex glove and stumbled opening a tube of lube, rubbing it along his index finger and smearing some over my ass hole.

'Just relax, I'm going to slip my finger in, this may be a little uncomfortable but it won't take long...'

'Take as long as you like...', I added cheekily.

The nurse chuckled...

I gasped as he went knuckle deep and squirmed his finger around until he felt my P spot, my little cocklette hardened and a bead of sissy cream oozed out. He rubbed over the area quite firmly and a spurt of sex cream ejaculated from my semi erect cocklette.

'Sorry about that....', I said embarrassingly...

'Oh it's ok, I'm just checking for any hardness or lumpy texture...', he explained.

'It's definitely hard...', I jokingly added.

He rubbed even more firmly, another squirt of ejaculate erupted from my swollen gurly cocklette, I let out a little stifled gasp of joy!

'Yes I can see you are, you're quite sensitive there, any pain?', he enquired.

'No pain, just intense pleasure....', I was just being honest.

'Right, all done, slip your knickers back on, ah you're not wearing any....', he added embarrassingly.

The nurse left and I adjusted my skirt, came from behind the curtain, noticed my cocklette was forming a little tent at the front, sat back at his desk, he clearly noticed also, gazing down between my thighs.

He wrote a few notes on my file and told me everything felt OK down there but he was sending me for an MRI just to be sure.

He asked me how my hormone treatment was going and complimented me on my figure, adding he had assumed I was a biological female. Which I took as a massive compliment.

I left the docs feeling elated and happy my examination was OK.

A few weeks later in a bar, I met the same locum doctor, he came over, 'oh hi, you're errm...', he couldn't remember, 'Fliss..', I helped his memory, 'that's it....err...how could I forget, you were my first patient..and most attractive....how are you?'

'Oh wow, really?', once again I was flattered, 'I'm fine, how about you?'

'Oh just drowning my sorrows with friends but they've all drifted off home..', he said seeming rather low.

'What's happened, tell Fliss all about it, a problem shared and all that....', I held his hand while he went on to explain he'd split with his gf, they had been engaged to be married, living together and he found out she was cheating.

I told him it was better he found out now, rather than years into their relationship, I called her a bitch and added she's lost a really nice guy, attractive, charming, funny, great at fingering my ass and those pecs, I stood back and admired, 'have you been hitting the gym?', he smiled and asked what I was drinking.

We had a few more drinks there, put the world to rights and went on to a club, danced off the rest of the night into the early morning.

He invited me back to his for coffee, never did make me one but woke up in his bed the next morning, he was naked next to me, his cock still hard, a trickle of cum oozing from my gaping ass, he'd certainly given my prostate another thorough workout that's for sure only not with just his finger this time!

Not only was I his first patient, I was his first man he'd slept with....I was truly honoured, blessed and felt special. 😘💋
 
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