First time sissy part 1 - parking lot BJ
So the first time I was with Daddy Richard I was not fully dressed. But I guess I should back up a little first. He responded to my post on Reddit about wanting to experiment with a dom and having some sissy fantasies but being inexperienced. He said he was in his mid 50's, in shape and looking to top/dom a regular sissy. He was also okay with the fact that I was both married, in my 40s and very closeted about this.
He and I would chat pretty often about fantasies. He was a typical daddy type of a man, assertive, cocky and confident - all things I liked. But unlike many others I had chatted with, he wasn't overly pushy about wanting to meet me so I actually had a good time whenever we talked.
Over time things eventually went into us discussing the possibility of meeting up. Since I felt comfortable enough that he wouldn't be some serial killer, I went with it and we planned to meet at the parking lot of a local mall to see if we had chemistry. At this point it pretty obvious that something sexual was going to happen between us, but we didn't really plan anything beforehand other than he wanted me to wear a pair of my wife's panties under my work clothes. He also said not to jerk off, and if I could get away with it, to shave my legs.
I was nervous all week thinking about it and I told my boss that I would be going to a dentist appointment that day so that I would have a little extra time if needed. After nervously driving around for a bit I parked my car near the food court and shortly after, Richard pulled up next to me, rolled his tinted window down and then motioned for me to get in.
I exited my car and hopped into his passenger seat. He smiled at me and I was relieved to see that he was actually the same person as in his pictures - good looking, confident and well dressed. We made small talk (or it was mostly him talking since I felt really nervous) and he drove us further back into the parking lot.
After driving around for a few minutes he put his hand on my thigh and gently rubbed it and asked if we should go to somewhere more private and I said sure. I knew what was going to happen and since he seemed like a nice person I agreed. He drove us into the parking garage where it was pretty empty.
After parking, he told me to relax. I think he could sense that I was nervous and embarrassed.
"Did you wear the panties like I asked? he asked me.
"Yes," I said.
"Yes, what?"
"Yes, Sir." I said.
"Good girl. Show me."
I nervously unzipped my slacks and showed him that I had a pair of black panties on with lace trim.
"Pull your pants down, Rachael," he said, using my girl name for the first time.
I did as told and pulled my pants down around my knees and he said to pull them all the way down to my ankles. I looked around to make sure there was no one else around and Richard laughed.
"Don't worry, sissy, we're alone."
Richard started caressing my thighs and then down my calves and ankles with his strong hands and complimented my legs. "You really do have very girly legs, Rachael. I bet your wife is jealous," he teased.
I didn't know what to say but enjoyed him feeling me up. My breathing was heavy and he could tell I liked it. He reached his hand back to my ass and gave it a hard squeeze. Eventually he reached my crotch. By that point I was already rock hard. He squeezed my clitty a couple of times which caused me to moan and then he did something I didn't expect and grabbed my balls and squeezed them firmly. This made me gasp in pain and look at him.
"Did you not jerk your clitty like I asked?" he asked.
"Yes..." I replied in pain.
He squeezed harder and I winced.
"Yes what, Rachael?
"Yes, Sir!" I said.
"Good girl," he said and he released my balls.
He reached two fingers underneath my balls and started to massage my perineum through the panties like it was a clit. This caused me to bite my lip and moan. I closed my eyes and spread my legs as best I could as he did this.
"Tell me what you want, Rachael," he asked and continued to rub me aggressively.
"I..I..want your cock...Sir."
"Are you sure that's what you want, Rachael?" he asked and increased the pressure causing me to moan and arch my back.
"Yes, Sir!"
He stopped rubbing me and adjusted his seat back. He unzipped his pants and opened the fly, which revealed a very large and hard cock. He pulled it out from the waistband of his underwear and it flopped forward and then smacked back against his belly. Rock hard and hot to the touch.
He pulled me closer to him and I was still too nervous to make the first move but I couldn't take my eyes off of his cock. It was impressive. I could see his hard cock pointing up towards me. He took the lead and guided my hand onto his cock. Almost instinctively I just grabbed it and started to stroke it up and down.
Richard sighed and watched me do this, giving me a naughty grin.
"Kiss it, princess. Kiss the head and kiss your way down like a good girl." he said.
And I did. I held his hard cock in my hands and felt it twitch.It felt so big. I bent down and placed a soft kiss on the tip. Richard moaned and I did it again, kissing the head and then the shaft.I kissed the shaft again and further down with soft kisses and some hard ones that made a smacking noise.
Richard grabbed the back of my head and pulled me into his crotch so that his hard cock was smashed up against the side of my face. He rubbed his cock up and down my face a few times like he was dry humping my face.
"You like that, Rachael? Tell daddy," he said and moaned.
"Yes, Daddy..." I said with his cock rubbing up and down my face. "I like it..."
"Good girl," he said. "Put Daddy's cock in your mouth now, princess."
He let my head go and I took the tip of his cock in my mouth and sucked it, thinking about how I would see it in movies and what I thought would feel good. I remember that I felt light headed, realizing how fast it all was happening and that I there I was, in panties with a hard cock in my mouth in the front seat of a man's car in a dark parking garage.
I could hear the sucking sounds I was making in the car and Richard moaning. It sounded like a porno movie. The cock felt so hot in my mouth as I sucked and jerked it. I also tried right away to deep throat it, being something I fantasized about but obviously I couldn't get it too deep and I gagged. Richard liked that. He would put his hands on top of my head and push me down on his cock and thrust his hips up a few times, which would make me gag and spit all over. I made a mess and gasped for air when he stopped but he seemed to like that as well.
I kept on sucking him like that for a little while and I had to take couple of breaks because my jaw was sore. Thankfully, he understood but said I need more training. During breaks I jerked his cock and kissed it like before, all over his shaft and on the tip, licking it too and trying my best to kiss his balls, which he seemed to really like.
He kept calling me his "good girl" and "princess" and rubbing my back and giving me gentle encouragement while at the same time being a little rough. My own cock strained in my panties and was a little painful as i was desperate for relief.
He said he was getting close and I should be ready. I wasn't really sure what he wanted me to do since this was actually during one of the 'breaks', but once again he took the lead and pushed my head down on his cock and held me there while he pumped into my mouth. I gagged again and made those porno noises tried to pull my head up but he was a lot stronger than me and he held me down this time and fucked my mouth like he wanted and said to take it like a good girl.
Eventually I felt his cock spasm and twitch and could feel him spurt jet after jet of hit cum into my mouth and he grunted very loudly and held me down. Without thinking about it I instinctively swallowed his load and had to fight the urge to throw up. Not that I didn't like it but it was a shock as this was something we didn't discuss at all.
Once he finished he let me go and told me to clean my mess, which i did the best I could and kissed his cock gently when I thought i was done.
During all this my own cock was painfully hard in my panties, but after he was done, he just zipped up and drove me back to my car. I quickly fumbled to get my pants up and tried to make sure I didn't have any cum on my face. We didn't say much after but he said I was a good girl and that he wanted to train me again soon. After he left, I had to go home to masturbate immediately - it felt so good it was almost painful and almost a let down. I wanted more.
Even though it was a pretty one sided experience, I really enjoyed giving the blowjob to him and the way he treated me like a slutty girl. So much actually that I did end up meeting with him a few more times for what he called "practice" before we moved on to more.
Hope you enjoyed. Let me know if you would like to hear more.
He and I would chat pretty often about fantasies. He was a typical daddy type of a man, assertive, cocky and confident - all things I liked. But unlike many others I had chatted with, he wasn't overly pushy about wanting to meet me so I actually had a good time whenever we talked.
Over time things eventually went into us discussing the possibility of meeting up. Since I felt comfortable enough that he wouldn't be some serial killer, I went with it and we planned to meet at the parking lot of a local mall to see if we had chemistry. At this point it pretty obvious that something sexual was going to happen between us, but we didn't really plan anything beforehand other than he wanted me to wear a pair of my wife's panties under my work clothes. He also said not to jerk off, and if I could get away with it, to shave my legs.
I was nervous all week thinking about it and I told my boss that I would be going to a dentist appointment that day so that I would have a little extra time if needed. After nervously driving around for a bit I parked my car near the food court and shortly after, Richard pulled up next to me, rolled his tinted window down and then motioned for me to get in.
I exited my car and hopped into his passenger seat. He smiled at me and I was relieved to see that he was actually the same person as in his pictures - good looking, confident and well dressed. We made small talk (or it was mostly him talking since I felt really nervous) and he drove us further back into the parking lot.
After driving around for a few minutes he put his hand on my thigh and gently rubbed it and asked if we should go to somewhere more private and I said sure. I knew what was going to happen and since he seemed like a nice person I agreed. He drove us into the parking garage where it was pretty empty.
After parking, he told me to relax. I think he could sense that I was nervous and embarrassed.
"Did you wear the panties like I asked? he asked me.
"Yes," I said.
"Yes, what?"
"Yes, Sir." I said.
"Good girl. Show me."
I nervously unzipped my slacks and showed him that I had a pair of black panties on with lace trim.
"Pull your pants down, Rachael," he said, using my girl name for the first time.
I did as told and pulled my pants down around my knees and he said to pull them all the way down to my ankles. I looked around to make sure there was no one else around and Richard laughed.
"Don't worry, sissy, we're alone."
Richard started caressing my thighs and then down my calves and ankles with his strong hands and complimented my legs. "You really do have very girly legs, Rachael. I bet your wife is jealous," he teased.
I didn't know what to say but enjoyed him feeling me up. My breathing was heavy and he could tell I liked it. He reached his hand back to my ass and gave it a hard squeeze. Eventually he reached my crotch. By that point I was already rock hard. He squeezed my clitty a couple of times which caused me to moan and then he did something I didn't expect and grabbed my balls and squeezed them firmly. This made me gasp in pain and look at him.
"Did you not jerk your clitty like I asked?" he asked.
"Yes..." I replied in pain.
He squeezed harder and I winced.
"Yes what, Rachael?
"Yes, Sir!" I said.
"Good girl," he said and he released my balls.
He reached two fingers underneath my balls and started to massage my perineum through the panties like it was a clit. This caused me to bite my lip and moan. I closed my eyes and spread my legs as best I could as he did this.
"Tell me what you want, Rachael," he asked and continued to rub me aggressively.
"I..I..want your cock...Sir."
"Are you sure that's what you want, Rachael?" he asked and increased the pressure causing me to moan and arch my back.
"Yes, Sir!"
He stopped rubbing me and adjusted his seat back. He unzipped his pants and opened the fly, which revealed a very large and hard cock. He pulled it out from the waistband of his underwear and it flopped forward and then smacked back against his belly. Rock hard and hot to the touch.
He pulled me closer to him and I was still too nervous to make the first move but I couldn't take my eyes off of his cock. It was impressive. I could see his hard cock pointing up towards me. He took the lead and guided my hand onto his cock. Almost instinctively I just grabbed it and started to stroke it up and down.
Richard sighed and watched me do this, giving me a naughty grin.
"Kiss it, princess. Kiss the head and kiss your way down like a good girl." he said.
And I did. I held his hard cock in my hands and felt it twitch.It felt so big. I bent down and placed a soft kiss on the tip. Richard moaned and I did it again, kissing the head and then the shaft.I kissed the shaft again and further down with soft kisses and some hard ones that made a smacking noise.
Richard grabbed the back of my head and pulled me into his crotch so that his hard cock was smashed up against the side of my face. He rubbed his cock up and down my face a few times like he was dry humping my face.
"You like that, Rachael? Tell daddy," he said and moaned.
"Yes, Daddy..." I said with his cock rubbing up and down my face. "I like it..."
"Good girl," he said. "Put Daddy's cock in your mouth now, princess."
He let my head go and I took the tip of his cock in my mouth and sucked it, thinking about how I would see it in movies and what I thought would feel good. I remember that I felt light headed, realizing how fast it all was happening and that I there I was, in panties with a hard cock in my mouth in the front seat of a man's car in a dark parking garage.
I could hear the sucking sounds I was making in the car and Richard moaning. It sounded like a porno movie. The cock felt so hot in my mouth as I sucked and jerked it. I also tried right away to deep throat it, being something I fantasized about but obviously I couldn't get it too deep and I gagged. Richard liked that. He would put his hands on top of my head and push me down on his cock and thrust his hips up a few times, which would make me gag and spit all over. I made a mess and gasped for air when he stopped but he seemed to like that as well.
I kept on sucking him like that for a little while and I had to take couple of breaks because my jaw was sore. Thankfully, he understood but said I need more training. During breaks I jerked his cock and kissed it like before, all over his shaft and on the tip, licking it too and trying my best to kiss his balls, which he seemed to really like.
He kept calling me his "good girl" and "princess" and rubbing my back and giving me gentle encouragement while at the same time being a little rough. My own cock strained in my panties and was a little painful as i was desperate for relief.
He said he was getting close and I should be ready. I wasn't really sure what he wanted me to do since this was actually during one of the 'breaks', but once again he took the lead and pushed my head down on his cock and held me there while he pumped into my mouth. I gagged again and made those porno noises tried to pull my head up but he was a lot stronger than me and he held me down this time and fucked my mouth like he wanted and said to take it like a good girl.
Eventually I felt his cock spasm and twitch and could feel him spurt jet after jet of hit cum into my mouth and he grunted very loudly and held me down. Without thinking about it I instinctively swallowed his load and had to fight the urge to throw up. Not that I didn't like it but it was a shock as this was something we didn't discuss at all.
Once he finished he let me go and told me to clean my mess, which i did the best I could and kissed his cock gently when I thought i was done.
During all this my own cock was painfully hard in my panties, but after he was done, he just zipped up and drove me back to my car. I quickly fumbled to get my pants up and tried to make sure I didn't have any cum on my face. We didn't say much after but he said I was a good girl and that he wanted to train me again soon. After he left, I had to go home to masturbate immediately - it felt so good it was almost painful and almost a let down. I wanted more.
Even though it was a pretty one sided experience, I really enjoyed giving the blowjob to him and the way he treated me like a slutty girl. So much actually that I did end up meeting with him a few more times for what he called "practice" before we moved on to more.
Hope you enjoyed. Let me know if you would like to hear more.
4 years ago
