Being a mans first time

[Sissy_LoriLux]

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.

 

[drobert44]

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.

Good and lucky sissy!

 

[Sissy_LoriLux]

I'll share another story.

I was 21 and the man was 32. I was dressed up in a hotel. He was bicurious but also married. He wanted oral.

He was afraid of meeting someone he knew so he asked if I could blindfold myself and wait on the floor on my knees. I said I could. I put the deadbolt out. Got on my knees on the floor and used a black stocking and tied it across my eyes.

He was waiting in the parking lot and came in my room right away. I heard him walk up unzip and a hard cock against my lips. I opened up and began to suck his cock. After about a minute he said "fuck it take the blindfold off" I did as I was told. He was handsome. I looked up at him while servicing his cock and he maintained eye contact.

"Do you have any condoms?" He asked. "No" I informed him. I continued sucking. He started to squirm a bit and I could taste a lot of precum.

"Bend over on the bed" he said. I got on all fours with my ass hanging over the edge of the bed. He lifted my dress and pulled down my panties. He began groping my ass his fingers touching my hole. I wrapped my hands around and spread my cheeks. He began slapping his cock against my hole. I pushed back each time. "Fuck it" he said.

He slid his cock into my ass and began fucking me. Immediately I could feel he was close. He would edge himself by pulling out and slapping his cock on my hole. One time he pulled out and shot a big rope of hot cum on my hole. He pushed it into me and blew a big load.

Last I talked to him he was actually dressing now and says the experience inspired him.

 

[Trubbycat]

I'd probably blow my load from sheer excitement...

 

[cruiser_2015]

I was mid twenties and he was fifties. He lived in the same apartment block as me. We met somehow and got friendly. We were both lonely and sexually frustrated. He invited me to his apartment. We chatted and looked af porn magazines. He started touching my thigh and bum and I didnt protest.

One night there were gay porn magazines in his collection. He asked me if I would strip for him and show him my cock. I was frustrated and Id done cock play with boys before. I thought what the hell and stripped to my briefs. I was up rock hard erect. I let him take my briefs off. I stood there wide legged with my hips rammed forward.

That time he just had a good feel of my naked cock, balls and bum and he hand-jobbed me off. He got his cock out and I jerked him off. On later meetings we sucked and frotted.

He was mostly into voyeur sex. He liked me to do erotic nude poses or pose in womens panties and slowly peel them off. He liked to watch me masturbate. Then he would jerk off over me while his spare hand played with me. He would splash his spurted semen over me.

He was kinky but fun and very satisfying at the time.

 

[Sissy_LoriLux]

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

 

[HotLoadLover]

...
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.

Just my observation, but making a 65-year old cum within a minute of penetration says a LOT for how turned on you got him !! You rocked his motherfucking world !!

 

[remington123691]

I've never had the opertunity to be some guys first but I'm holding out hope!

 

[BillyWalrus]

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

With a pretty face like yours, gay straight bi, who cares. Who could blame any man for wanting to get in your pants?

 

[Trubbycat]

Just my observation, but making a 65-year old cum within a minute of penetration says a LOT for how turned on you got him !! You rocked his motherfucking world !!

I'm getting there agewise with a mild case of ED. Getting me hard enough to fuck would make me very happy and appreciative.

 

[Biguy77578]

I've never had the opertunity to be some guys first but I'm holding out hope!

In high-school I had a friend who moved in with me and my mother because he couldn't get along with his stepfather. We both had girlfriends and got a lot of pussy but one weekend he didn't get any and because we slept in the same bed and we were jacking off he said he could sure use a blow job. I told him I could help with that and blew him the first time. That became a routine when he didn't get layed. Sometime later he brought up he wanted to fuck his girlfriends ass but she refused and asked if I had ever been fucked. I lied and told him I hadn't but had thought about it. He asked if I wanted to try. I acted reluctant but finally agreed. In reality I had been fucked many times. I knew just what to do and greased his cock and my ass but told him to take it easy. I leaned over the side of the bed and he got behind me and positioned his cock at my hole. As he began to push I clenched my as closed and groaned like it hurt. I slowly relaxed and allowed him to enter. "I haven't mentioned he has a nice cock about 7" long and thick". He withdrew then started back in going beeper repeating until he bottomed out and began thrusting. It felt awsome. I pushed back as he trusted into me unt I l he groaned and came in my ass.

We fucked any time he needed relief. I wasn't too long before I got him to suck me and eventually I fucked him. But that's another stpry.

 

[stargame]

I can identify with all of these situations and stories. For me it was my neighbor, I would do some small chores for him around his house and garden. One day I was working in his garden pulling weeds, and I was wearing cute little shorts. I knew he was staring at my ass as I leaned over to pull weeds. And because it was hot outside, he invited me into the house for some ice water. Once in the house, he asked me to sit on his lap. I admit, I was curious, so as I was sitting on this lap, I noticed he was getting very hard. He wrapped his arms around me and started feeling my little breast through my unbuttoned shirt. It felt so good, and I guess I was wiggling and squirming on his lap. The cool house, the ice water, his hands on me; everything start to get very sensual. Then it happened. He pulled down his pants and out popped a gigantic hard cock. It was between my thighs. I'd never seen anything so big, as somehow I wiggled out of my shorts. He lifted me up by my waist and placed me on top of his hard manhood. I could feel him probing and searching and stabbing against my little tiny balls. Then, something amazing happened, suddenly I felt my neighbor stiffen up and grab my thighs. He creamed all over my cute little bare ass and thighs. I laid my head back on his shoulder, and I can feel him breathing hard and panting.

 

[Smoothshavendad]

I can identify with all of these situations and stories. For me it was my neighbor, I would do some small chores for him around his house and garden. One day I was working in his garden pulling weeds, and I was wearing cute little shorts. I knew he was staring at my ass as I leaned over to pull weeds. And because it was hot outside, he invited me into the house for some ice water. Once in the house, he asked me to sit on his lap. I admit, I was curious, so as I was sitting on this lap, I noticed he was getting very hard. He wrapped his arms around me and started feeling my little breast through my unbuttoned shirt. It felt so good, and I guess I was wiggling and squirming on his lap. The cool house, the ice water, his hands on me; everything start to get very sensual. Then it happened. He pulled down his pants and out popped at gigantic hard cock. It was between my thighs. I'd never seen anything so big, as somehow I wiggled out of my shorts. He lifted me up by my waist and placed me on top of his hard manhood. I could feel him probing and searching and stabbing against my little tiny balls. Then, something amazing happened, suddenly I felt my neighbor stiffen up and grab my thighs. He creamed all over my cute little bare ass and thighs. I laid my head back on his shoulder, and I can feel him breathing hard and panting.

Oh fuck!!!!!!

 

[remington123691]

I can identify with all of these situations and stories. For me it was my neighbor, I would do some small chores for him around his house and garden. One day I was working in his garden pulling weeds, and I was wearing cute little shorts. I knew he was staring at my ass as I leaned over to pull weeds. And because it was hot outside, he invited me into the house for some ice water. Once in the house, he asked me to sit on his lap. I admit, I was curious, so as I was sitting on this lap, I noticed he was getting very hard. He wrapped his arms around me and started feeling my little breast through my unbuttoned shirt. It felt so good, and I guess I was wiggling and squirming on his lap. The cool house, the ice water, his hands on me; everything start to get very sensual. Then it happened. He pulled down his pants and out popped at gigantic hard cock. It was between my thighs. I'd never seen anything so big, as somehow I wiggled out of my shorts. He lifted me up by my waist and placed me on top of his hard manhood. I could feel him probing and searching and stabbing against my little tiny balls. Then, something amazing happened, suddenly I felt my neighbor stiffen up and grab my thighs. He creamed all over my cute little bare ass and thighs. I laid my head back on his shoulder, and I can feel him breathing hard and panting.

Did you go back and do more?

 

[imustadmit]

There was an older guy that worked at the liquor store I frequented. This was years ago. He was always there every week when I'd go in. Over the course of months, we'd struck up a nice rapport, though I doubt he'd know what that word meant lol....

I asked him once whether he was married and he said no. I asked him if he had a gf and the answer was not currently. I asked him if he ever got his cock sucked, and i could see the pain in his eyes when he told me it had been a year since the last time.

I couldn't let this poor bastard wait, could I? I asked him if he'd ever had a guy suck him and he said no but, at this point, he would. We made arrangements.

His cock was bigger than I had thought it would be, a nice girthy 7". He was nervous at first, but that faded as a few minutes went by. I had to tell him that I admired his stamina since it been so long. And then I told him his cock was a challenge to suck it was so big. That made him go a bit feral! He grabbed the back of my head and pushed it down and just fucked my mouth til he came. Nice evening!

 

[Biguy77578]

I can identify with all of these situations and stories. For me it was my neighbor, I would do some small chores for him around his house and garden. One day I was working in his garden pulling weeds, and I was wearing cute little shorts. I knew he was staring at my ass as I leaned over to pull weeds. And because it was hot outside, he invited me into the house for some ice water. Once in the house, he asked me to sit on his lap. I admit, I was curious, so as I was sitting on this lap, I noticed he was getting very hard. He wrapped his arms around me and started feeling my little breast through my unbuttoned shirt. It felt so good, and I guess I was wiggling and squirming on his lap. The cool house, the ice water, his hands on me; everything start to get very sensual. Then it happened. He pulled down his pants and out popped at gigantic hard cock. It was between my thighs. I'd never seen anything so big, as somehow I wiggled out of my shorts. He lifted me up by my waist and placed me on top of his hard manhood. I could feel him probing and searching and stabbing against my little tiny balls. Then, something amazing happened, suddenly I felt my neighbor stiffen up and grab my thighs. He creamed all over my cute little bare ass and thighs. I laid my head back on his shoulder, and I can feel him breathing hard and panting.

Awsome. I had a couple of fun neighbors.

 

[TheIntrepidBoyager]

Can't tell about being a man's first as that hasn't really happened. But I could tell you about my first as a man.

 

[searchn469]

why is it so difficult to find a partner willing to take my anal cherry. have made the request a few times and it never happens. lot of promises but no success. ill eat their ass even suck their cock but once they have been satisfied, nothing happens. enjoy foreplay and have both of us stimulated and then they want me to take care of them. always seem to feel rejected

 

[Scooter58]

I love these stories. I’m getting hard just reading them!

 

[DickandDoof]

I love these stories. I’m getting hard just reading them!

I’ve gone way beyond hard just reading these stories.