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.