Jessies surprise part 2
- 3 years ago
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Jessie's Time For Payback free porn video
After Dan left me with his cum dripping out of my ass, I kept replaying his words before he left.
“Jessie, you were amazing! I can’t wait to tell all the guys at work about this!”
It was Friday night. Dan was the first one to make me feel like a woman, but now I had another dilemma. How am I going to face him and all of my co-workers if he indeed tells everyone about me?
I woke up Saturday and took a nice relaxing lavender salt bath. While soaking and exfoliating my skin, I reflected back on the events that happened the night before. Even though I fantasized about being a woman, and wondered what they felt while having sex, last night was quite unexpected. It was a serendipitous moment. I smiled while I replayed the events in my head.
Later in the day I went on a shopping spree. I usually like the more anonymous feel of online shopping, and today was no exception. Even with my new Red Riding Hood costume, I couldn’t resist looking at the women’s costumes at several online Halloween retailers. All of the hot sexy costumes were starting to get me more and more excited. I went to the clearance page and started to scroll through the discounted costumes. Then I found it. It was the costume that was the subject of many fantasies. It was the Slave Leia costume. My fantasies were of me enjoying a woman dressed up as Slave Leia, not of me dressed up as Slave Leia. But here I was, picking my size, and completing the check out.
Now that I was going to have another new hot sexy costume, I needed a new pair of shoes to go with it. After several searches, I found a pair of bronze colored strappy high heeled sandals. They were perfect for the costume, and the retailer had a size that would fit me. Another check-out, and another satisfied customer. The shopping spree definitely took my mind off of what might happen on Monday.
Monday came, and I was dreading going into work. The commute was painfully slow which only served to extend my agony. When I got into the office, there was nothing out of the unusual. I sat down in front of my computer and checked my e-mails. There was one waiting for me that was from Dan with ";)" as the subject matter. I hesitated to open it up, but in the same token, I had to know what he sent me.
Jessie,
Thanks for having me over to celebrate our achievement last week. You sure know how to celebrate!
Dan
Okay, not too bad. On Wednesday, I was walking down the hallway when I thought I heard Dan say, “and I was the big, bad, wolf,” to Zach and Aaron. As I walked by them, there weren’t any snickers or stares, so I thought to myself that I'd misheard Dan.
The rest of the week was uneventful, so I felt pretty good that maybe this would blow over and only Dan would know my secret. At least it was uneventful until Friday.
On Friday afternoon, I received another e-mail from Dan.
Jessie,
I’ve been thinking about last week a lot, and I would like to continue our celebration tonight at my place. Be there at 8pm.
Dan
It was now Friday evening, and I drove over to Dan’s house as Jesse, my male self. I walked up to the front door and heard several voices. I rang the door bell, and Dan answered. “Come in Jesse! Now the party can start!”
I walked in and saw Zach and Aaron enjoying a beer. “Jesse!” they said in unison.
I replied, “Hey Zach and Aaron!”
I sat down and had a beer as well. We talked a lot about the work week and how there is another big project that will be starting shortly. After a while, the subject went on to some of the hot women at our work, and honest talk about who we would want to have sex with. Eventually it rolled back to Dan who was a little quiet during the conversation. Dan told us, that there was a woman that he had sex with recently, and her ass was amazing. He went into detail of how she clamped her legs around him so he had no choice but to unload in her ass. As he was stating this, he looked right at me and smiled. That same look of horror came over my face.
Dan proceeded to say that he'd invited her to come over tonight to have some fun with some more co-workers.
“I’ve always had a fantasy to have sex with a woman wearing this.” Dan pulled out two packages and I immediately turned bright red. It was my Slave Leia costume and high heels that I'd ordered the weekend before. Both Zach and Aaron wolf whistled their appreciation of the costume and high fived each other.
Dan looked right at me and said, “It’s time for payback.” He handed me the package.
Dan directed me upstairs into his room where several other items were waiting for me. There was a wig with a long braided ponytail, a makeup set, and a pair of thigh high nude pantyhose. Before he left me alone, he said, “I want you to get ready to serve us tonight. If you don’t, I’ll share the photos that I took of you in a very compromising position.”
I quickly put on make-up, the Slave Leia costume, and neck choker with chain. Next were the nude pantyhose, of which I took special attention to not run them. Finally I put on my bronze colored strappy high heels. I looked in the mirror and realized I might be able to pass as a woman if I could apply make-up skillfully. Finally, I walked downstairs as sexily as I possibly could. Even though I was embarrassed, some of the same thoughts of wanting to be a complete woman entered my mind. I turned the corner into the living room and Zach laid his eyes on me first. “Oh my god! Dan! You’re right! Jessie looks hot as a woman!”
I had an unsure smile from the compliment, but it did boost my confidence. Aaron turned to look at me, and his reaction was equally reassuring. Finally, as Dan grabbed my chain he said, “Come here slave. It is time for your payback. Zach and Aaron, be prepared for a night to remember!”
Dan tugged me closer to him and he stuck his tongue into my mouth. It wasn’t the same passionate kiss like the week prior, but a harder more dominating kiss. My inhibitions were waning quickly, and I was starting to get hot and horny. Dan finally released me and I noticed Zach and Aaron already had their cocks out and were stroking them. I knew right then that this would not be a night of passion, but a night of pure lust.
Zach grabbed my chain and tugged me toward him. “Alright Slave Jessie, it is time for some lip service.” With that, he pushed me onto my knees and started to push his cock toward my face. I took his cock in my hands and started to stroke him. Zach, becoming impatient, pushed my head on to his cock. When the head got to my lips, there was a little drop of pre-cum at the tip, so I stuck my tongue out so I could savor its taste before he used my mouth as a hole to enjoy.
After a couple of minutes, Zach started thrusting his cock into my mouth. Every once in a while I would gag when the head of his cock reached the back of my throat. Eventually, I managed to relax as I started getting used to him in my mouth. While all this was happening, I heard Aaron state to Dan that I was a very obedient slave and that he was lucky to have found out my secret love of cross-dressing. After a couple of minutes of observing Zach fucking my mouth, Aaron said, “It is time for me to get a piece of slave ass!”
Aaron lifted my backside, quickly moved my Slave Leia panties aside, and pointed the tip of his manhood at the entrance of my ass. I was expecting some lube to be applied to my rear, however I was wrong. Aaron quickly shoved his manliness inside of me in one fell swoop. There was no time to get used to him, no sense of him treating me like a woman. It was just pure animal instinct and lust. Several tears came out of my eyes from the sharp pain of the unexpected entrance into my backside.
So now for the first time in my life, I was on my hands and knees with two cocks inside of me. Aaron placed both of his hands around my waist and gripped hard in order to ensure he could thrust himself deeply inside of me. Both Zach and Aaron found a rhythm where I started to rock back and forth, which maximized their penetration into me. Aaron shifted his position a little which put pressure on my male G spot. This new sensation caused my cock to harden like steel. I was totally lost in the pleasure of being taken like a slave. Both Zach and Aaron were really getting into it and started calling me names like slut, cocksucker, and sissy boy. Hearing those words got me more hot and horny, and I realized that I was quickly turning into all of those.
After fifteen minutes of continuous double dicking, Zach and Aaron started moaning and saying they were going to cum soon. Dan told them that I was a cum slut, and that they should shoot their loads deeply inside of me. I was going to have another first, and it filled my mind with a little fear, but mostly with curiosity and excitement. While Zach and Aaron were building up to their climax, mine hit me very suddenly, and hard. I moaned with Zach’s cock in my mouth as my own cum started shooting out into my Slave Leia panties. The vibrations from my moaning set Zach over the edge, and he shot spurt after spurt of cum into my mouth. Zach told me to not swallow, but keep it in my mouth. He filled me with so much cum that some of it dribbled past my lips and down my chin.
During my orgasm, my ass clamped hard onto Aaron’s cock. Aaron yelled out in excitement, “Take my full load inside your ass, Slave Jessie!” With that, he shot load after load inside of me. Dan seeing me as a total slave slut, told Aaron to keep inside of me for a minute.
Dan then lifted my face toward him and said, “Open your mouth and show me all of the cum in your mouth.” I opened my mouth and showed him the pearly white load.
“Good job my Slave Jessie. Now I want you to swallow it, and prove to me you swallowed.” I did exactly as he said.
“Now I see that you made Aaron a little messy. I think you need to clean him off,” Dan said.
Aaron removed his cock from my backside and streams of cum immediately poured out of me. He then turned me around and stuck himself inside my mouth. I cleaned him and tasted two distinct flavors. It was dirty, it was odd, but in some strange way it tasted good. After cleaning him up, he removed his cock from my mouth and moved over to Zach. They gave each other a high five and Aaron said, “Jessie, your ass is so perfect. I think you have what it takes to satisfy any man.” I glowed inside from the compliment.
I got up from being on my hands and knees and started to leave the room. I figured it was time to get dressed and go home. Suddenly there was a tug from the neck chocker around my neck. I stopped dead in my tracks and fell to my knees.
“Where do you think you’re going?” Dan asked.
Dan continued, “We are not done with our Slave Jessie. We are just getting started!”
Dan, Zach, and Aaron gave each other more high fives and patted each other on their shoulders. I remained on my knees with cum dripping down my thighs wondering what is in store for me.
“Jessie, you were amazing! I can’t wait to tell all the guys at work about this!”
It was Friday night. Dan was the first one to make me feel like a woman, but now I had another dilemma. How am I going to face him and all of my co-workers if he indeed tells everyone about me?
I woke up Saturday and took a nice relaxing lavender salt bath. While soaking and exfoliating my skin, I reflected back on the events that happened the night before. Even though I fantasized about being a woman, and wondered what they felt while having sex, last night was quite unexpected. It was a serendipitous moment. I smiled while I replayed the events in my head.
Later in the day I went on a shopping spree. I usually like the more anonymous feel of online shopping, and today was no exception. Even with my new Red Riding Hood costume, I couldn’t resist looking at the women’s costumes at several online Halloween retailers. All of the hot sexy costumes were starting to get me more and more excited. I went to the clearance page and started to scroll through the discounted costumes. Then I found it. It was the costume that was the subject of many fantasies. It was the Slave Leia costume. My fantasies were of me enjoying a woman dressed up as Slave Leia, not of me dressed up as Slave Leia. But here I was, picking my size, and completing the check out.
Now that I was going to have another new hot sexy costume, I needed a new pair of shoes to go with it. After several searches, I found a pair of bronze colored strappy high heeled sandals. They were perfect for the costume, and the retailer had a size that would fit me. Another check-out, and another satisfied customer. The shopping spree definitely took my mind off of what might happen on Monday.
Monday came, and I was dreading going into work. The commute was painfully slow which only served to extend my agony. When I got into the office, there was nothing out of the unusual. I sat down in front of my computer and checked my e-mails. There was one waiting for me that was from Dan with ";)" as the subject matter. I hesitated to open it up, but in the same token, I had to know what he sent me.
Jessie,
Thanks for having me over to celebrate our achievement last week. You sure know how to celebrate!
Dan
Okay, not too bad. On Wednesday, I was walking down the hallway when I thought I heard Dan say, “and I was the big, bad, wolf,” to Zach and Aaron. As I walked by them, there weren’t any snickers or stares, so I thought to myself that I'd misheard Dan.
The rest of the week was uneventful, so I felt pretty good that maybe this would blow over and only Dan would know my secret. At least it was uneventful until Friday.
On Friday afternoon, I received another e-mail from Dan.
Jessie,
I’ve been thinking about last week a lot, and I would like to continue our celebration tonight at my place. Be there at 8pm.
Dan
It was now Friday evening, and I drove over to Dan’s house as Jesse, my male self. I walked up to the front door and heard several voices. I rang the door bell, and Dan answered. “Come in Jesse! Now the party can start!”
I walked in and saw Zach and Aaron enjoying a beer. “Jesse!” they said in unison.
I replied, “Hey Zach and Aaron!”
I sat down and had a beer as well. We talked a lot about the work week and how there is another big project that will be starting shortly. After a while, the subject went on to some of the hot women at our work, and honest talk about who we would want to have sex with. Eventually it rolled back to Dan who was a little quiet during the conversation. Dan told us, that there was a woman that he had sex with recently, and her ass was amazing. He went into detail of how she clamped her legs around him so he had no choice but to unload in her ass. As he was stating this, he looked right at me and smiled. That same look of horror came over my face.
Dan proceeded to say that he'd invited her to come over tonight to have some fun with some more co-workers.
“I’ve always had a fantasy to have sex with a woman wearing this.” Dan pulled out two packages and I immediately turned bright red. It was my Slave Leia costume and high heels that I'd ordered the weekend before. Both Zach and Aaron wolf whistled their appreciation of the costume and high fived each other.
Dan looked right at me and said, “It’s time for payback.” He handed me the package.
Dan directed me upstairs into his room where several other items were waiting for me. There was a wig with a long braided ponytail, a makeup set, and a pair of thigh high nude pantyhose. Before he left me alone, he said, “I want you to get ready to serve us tonight. If you don’t, I’ll share the photos that I took of you in a very compromising position.”
I quickly put on make-up, the Slave Leia costume, and neck choker with chain. Next were the nude pantyhose, of which I took special attention to not run them. Finally I put on my bronze colored strappy high heels. I looked in the mirror and realized I might be able to pass as a woman if I could apply make-up skillfully. Finally, I walked downstairs as sexily as I possibly could. Even though I was embarrassed, some of the same thoughts of wanting to be a complete woman entered my mind. I turned the corner into the living room and Zach laid his eyes on me first. “Oh my god! Dan! You’re right! Jessie looks hot as a woman!”
I had an unsure smile from the compliment, but it did boost my confidence. Aaron turned to look at me, and his reaction was equally reassuring. Finally, as Dan grabbed my chain he said, “Come here slave. It is time for your payback. Zach and Aaron, be prepared for a night to remember!”
Dan tugged me closer to him and he stuck his tongue into my mouth. It wasn’t the same passionate kiss like the week prior, but a harder more dominating kiss. My inhibitions were waning quickly, and I was starting to get hot and horny. Dan finally released me and I noticed Zach and Aaron already had their cocks out and were stroking them. I knew right then that this would not be a night of passion, but a night of pure lust.
Zach grabbed my chain and tugged me toward him. “Alright Slave Jessie, it is time for some lip service.” With that, he pushed me onto my knees and started to push his cock toward my face. I took his cock in my hands and started to stroke him. Zach, becoming impatient, pushed my head on to his cock. When the head got to my lips, there was a little drop of pre-cum at the tip, so I stuck my tongue out so I could savor its taste before he used my mouth as a hole to enjoy.
After a couple of minutes, Zach started thrusting his cock into my mouth. Every once in a while I would gag when the head of his cock reached the back of my throat. Eventually, I managed to relax as I started getting used to him in my mouth. While all this was happening, I heard Aaron state to Dan that I was a very obedient slave and that he was lucky to have found out my secret love of cross-dressing. After a couple of minutes of observing Zach fucking my mouth, Aaron said, “It is time for me to get a piece of slave ass!”
Aaron lifted my backside, quickly moved my Slave Leia panties aside, and pointed the tip of his manhood at the entrance of my ass. I was expecting some lube to be applied to my rear, however I was wrong. Aaron quickly shoved his manliness inside of me in one fell swoop. There was no time to get used to him, no sense of him treating me like a woman. It was just pure animal instinct and lust. Several tears came out of my eyes from the sharp pain of the unexpected entrance into my backside.
So now for the first time in my life, I was on my hands and knees with two cocks inside of me. Aaron placed both of his hands around my waist and gripped hard in order to ensure he could thrust himself deeply inside of me. Both Zach and Aaron found a rhythm where I started to rock back and forth, which maximized their penetration into me. Aaron shifted his position a little which put pressure on my male G spot. This new sensation caused my cock to harden like steel. I was totally lost in the pleasure of being taken like a slave. Both Zach and Aaron were really getting into it and started calling me names like slut, cocksucker, and sissy boy. Hearing those words got me more hot and horny, and I realized that I was quickly turning into all of those.
After fifteen minutes of continuous double dicking, Zach and Aaron started moaning and saying they were going to cum soon. Dan told them that I was a cum slut, and that they should shoot their loads deeply inside of me. I was going to have another first, and it filled my mind with a little fear, but mostly with curiosity and excitement. While Zach and Aaron were building up to their climax, mine hit me very suddenly, and hard. I moaned with Zach’s cock in my mouth as my own cum started shooting out into my Slave Leia panties. The vibrations from my moaning set Zach over the edge, and he shot spurt after spurt of cum into my mouth. Zach told me to not swallow, but keep it in my mouth. He filled me with so much cum that some of it dribbled past my lips and down my chin.
During my orgasm, my ass clamped hard onto Aaron’s cock. Aaron yelled out in excitement, “Take my full load inside your ass, Slave Jessie!” With that, he shot load after load inside of me. Dan seeing me as a total slave slut, told Aaron to keep inside of me for a minute.
Dan then lifted my face toward him and said, “Open your mouth and show me all of the cum in your mouth.” I opened my mouth and showed him the pearly white load.
“Good job my Slave Jessie. Now I want you to swallow it, and prove to me you swallowed.” I did exactly as he said.
“Now I see that you made Aaron a little messy. I think you need to clean him off,” Dan said.
Aaron removed his cock from my backside and streams of cum immediately poured out of me. He then turned me around and stuck himself inside my mouth. I cleaned him and tasted two distinct flavors. It was dirty, it was odd, but in some strange way it tasted good. After cleaning him up, he removed his cock from my mouth and moved over to Zach. They gave each other a high five and Aaron said, “Jessie, your ass is so perfect. I think you have what it takes to satisfy any man.” I glowed inside from the compliment.
I got up from being on my hands and knees and started to leave the room. I figured it was time to get dressed and go home. Suddenly there was a tug from the neck chocker around my neck. I stopped dead in my tracks and fell to my knees.
“Where do you think you’re going?” Dan asked.
Dan continued, “We are not done with our Slave Jessie. We are just getting started!”
Dan, Zach, and Aaron gave each other more high fives and patted each other on their shoulders. I remained on my knees with cum dripping down my thighs wondering what is in store for me.
Lianne
- 18.12.2021
- 35
- 0
- Category:
- Crossdressing
