Jessies surprise part 2
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Jessie's Fantasy Chapter 8: A New Beginning free porn video
I sat in stunned silence after the love of my life gave up my little secret to all of my friends. After losing a bet with John, I had to dress up as a woman and try to hook up with a guy as payment. Tracy and her friends did such a good job making me look like a woman, that I was able to fool all of my friends into having unplanned, but very much enjoyed, sex with me. It wasn’t until Ross and Steve had their turn with me that Tracy decided to announce to my friends who Jessie really was.
Tracy said, “Oh my god hun, you were amazing with these studs! I can’t believe that you actually let all of your friends fuck you and cum inside you!”
Fear and a slight moment of panic came across me. I wanted to run away and never see or confront my friends again. I was certain I would get the crap beaten out of me as a couple of my friends tended toward homophobia, and the sheer act of fooling them wouldn’t likely sit well with them.
Brian turned toward me in disbelief. “No way!!! There is no way that you are our friend Jesse. He doesn’t have a hot body like you do.”
“Or a sexy ass like you do!” piped in Scott.
I glanced at all of my friends and bowed my head down. I was about ready to cry. I slowly placed my hand on the back side of my head and unfastened two clips that held my wig to my natural hair, and pulled my wig off. Next, I removed my dress and turned to face them. My poor deflated boy clit was noticeable for all to see.
As I lowered my face again, I replied to them. “Yes. This is me, Jesse.”
Mark came up to me. I cowered a little as I was certain he was going to be the one that would kick my ass. He placed his hand on my cheek and lifted my face so our eyes would meet. I didn’t see any anger on his face. All I saw was one of bewilderment and confusion. After many seconds of him staring deep into my eyes and pure silence, he spoke.
“Jessie, you are one of the hottest, most sensual creatures I have ever been with. I would never in a million years guessed that you were my male friend Jesse.”
With that, he proceeded to kiss me. I was in complete shock of this turn of events. We kissed for what seemed like many minutes, and I noticed my tension and fear melted away.
Tracy pushed Mark aside and stated to him, “Don’t get too attached to Jessie. She is mine.”
What followed was several hours of my friends and I talking about the events that had unfolded over the last couple of days. There was question after question about what I felt, did I like it, who was the best, would I have sex like this again? So many questions came my way. It was all very respectful and they were treating me like a lady.
It was odd, as I was a total slut for them. But two things were certain. First, not a single one of my friends suspected at the time that I was following up on my payment. Second, I knew our friendships would never be the same, but at least I knew that they would still be friends of mine. After all of the questions and conversation, there was still the elephant in the room that no one dared to ask. Did I like it enough to continue to be Jessie and give up my life as a male? As Tracy and I were getting up to leave, Ross asked one final question.
“Jessie, what will happen after tonight? Are you going to be our male friend Jesse, or is he gone forever?”
I replied, “I’m really not sure right now.”
On the drive home with Tracy, I was a mix of emotions and conflict. We talked the entire time in the car about my future and what my plans were going to be. Let’s just say that I kept going back and forth as there were aspects of my male self that I enjoyed, and there were female aspects I enjoyed. I told Tracy, I needed to do some soul searching before I conclude what my future would look like.
Throughout the week, I continued to wear cute panties under my work clothes as male underwear, for some reason, didn’t appeal to me in the least. I really never thought of it at the time, but my mind was truly made up. That weekend, Tracy dressed me up in sexy lingerie and we made love for hours on end. It was a weekend where neither of us wanted to get out of bed. We just enjoyed exploring each other and learning how to please each other the most. I have to say that our love making was very soft, and we took our time. It was some of the most erotic and most satisfying sex that we had since we became a couple.
As the next couple of weeks went on, I started enjoying my feminine side, which meant that I always wore panties to work, and removed all traces of my male self once I got home. My phone would ring, yet I wouldn’t answer it seeing it was one of my friends. Tracy and I were still intimate with each other, but I noticed that something seemed off with her, especially when we started making love in the morning. When I brought it up to Tracy, she changed the subject.
“Hun, I know you are ignoring your friends. They really don’t deserve that. Please go out with them this weekend.”
“I don’t know,” I replied.
I started getting emotional. It was odd, but the last week I felt very emotional for some reason. This wasn’t like me in the least.
“Please call them up and talk to them.” She repeated.
I called up Brian and talked to him. After the conversation, I turned to Tracy and told her I was going to go out with my friends tonight.
Tracy smiled and said, “Oh good! I am so glad you decided to go with your friends. I’ll make sure I dig up some of your casual clothes to wear.”
I turned to her and stated, “That won’t be necessary. I would like to wear something sexy.”
Tracy looked at me and smiled.
Work seemed to drag by. I just couldn’t wait until 4PM when I would head home and get ready for a night out with my friends. When it was finally time to leave, I called up Tracy and let her know I was heading home.
After a fairly decent commute, I got home and opened the door. “Hunny! I’m home!”
Unlike every night that I came home, Tracy didn’t answer. I yelled it again, and still no answer. I walked into the kitchen and saw Tracy with her two friends Suzy and Brooke sitting around the kitchen table.
“Hi, Hun! So sorry. I didn’t hear you come in.”
“That’s OK hun. Hi, Suzy and Brooke! What’s the occasion?” I asked.
Tracy opened the conversation “Do you remember our first night together?”
“Of course I do. It was the day I approached you with my quandary. Why?”
Brooke added, “and what happened between you and Tracy?”
“Well, I remember that we had some amazing sex in the bathtub. I met you and Suzy, and... ”
Suzy interrupted, “No need to explain the entire night. So you had sex with Tracy.”
“Yes, it was amazing, and that’s when I proclaimed I loved her,” I replied.
With a big smile on her face, she said, “Hunny? I’m pregnant!”
A look of shock came across my face. Pregnant? Did the love of my life say pregnant? I certainly must be hearing things.
I finally stated the words, “Pregnant? Really? We are going to be parents?”
Tracy gave me a big kiss and said, “No.”
A look of confusion came across my face.
Tracy stated, “Not just you and I.”
I was so confused by what Tracy was saying. I started crying with joy as I hugged Tracy and started proclaiming “I’m going to be a mom!”
Tracy interrupted my happy thoughts with, “Did you hear what I said?”
“Yes, hun! We are going to be parents!”
“Yes, but it isn’t just you and I. We all are going to be parents.”
“I know! This is the best day of my life! You and I are going to have a baby together! This calls for a celebration!” I replied.
Suzy and Brooke just laughed and told Tracy, “Jessie doesn’t get it, does she?”
Tracy shrugged her shoulders, “No, she really doesn’t get it.”
I was so excited that couldn’t get my make-up on so I asked for Tracy and her friends to help me.
“I can’t wait to meet my friends and tell them the great news! I’m going to have a baby!”
Tracy, Brooke, and Suzy tried to get me to listen to their words, but I was on cloud nine. That only meant that I couldn’t comprehend what was really stated. After they helped get me ready, I kissed each of them goodbye and went to Brian’s house.
Mark and Ross were already at Brian’s house when I arrived. When Brian opened the door, his jaw just about dropped.
“Oh my god Jessie! You look so hot!”
Ross followed it up with a cat call whistle.
“Thanks, guys. You’ll never guess what I just found out! Tracy and I are expecting a baby!”
“What?” Ross questioned.
“Holy shit! Congratulations! Let’s go celebrate!” Mark shouted.
We went out to our usual hang out, only this time I was able to do so as my feminine self. We enjoyed the conversation and got a lot of laughs at the men that were hitting on me. I was feeling no pain from the celebration. This was a dangerous position for me as my inhibitions were weakening, and I was starting to flirt back to the men hitting on me.
Brian stated to me, “Jessie, we should get going and finish celebrating at my place.”
I whined, “But... But.. I like the attention I am getting.”
“You can get the same attention at a later time with Tracy,” Ross interjected.
We piled into Brian’s car and started to head back to his place. While in the back seat with Ross, I was getting frisky and started playing with his crotch. At first, Ross was pushing my hand away and stating he wanted to have fun with a real woman. It hurt my feelings to the point I was crying. I don’t understand what has been going on with my emotions lately, but damn they are so not the normal male Jesse emotions.
Ross wrapped his arms around me to comfort me, and said, “I didn’t mean to hurt you.”
When we got to Brian’s house, I was feeling happier, but also more horny. I made up my mind I was going to get into one of their pants tonight.
After many hours of conversation and my expressing my delight that I was going to be a mom for the umpteenth time, Ross and Mark left. As the fire was dying in the fireplace, I got a sudden chill so I snuggled in close to Brian. He wrapped his arms around me in an assuring way, but also bringing me closer to him. I smiled in content as he started rubbing my ass. I slowly moved my hand down to his crotch until I reached his zipper. With one slow and steady motion, I had opened the fly of his pants and reached in for my prize.
Brian looked at me and asked, “Are you sure Tracy is OK with this?”
I nodded and then moved my mouth over the tip of his nice hard shaft. Brian ever so slightly tensed up, but then relaxed as the warmth of my mouth surrounded his cock. “Mmmmm, Jessie. Where in the world did you learn to suck a cock? There is no way that you haven’t done it prior to losing your bet. You’re way too good at this.”
I paused and looked up at his eyes, “I never had another man inside of me prior to losing the bet.”
Brian couldn’t believe it. He let me continue sucking on his cock. No more words were said that night. It was just me making love to his nice hard shaft. I had put him on edge many times in order to build up his climax. After an hour of sucking him off, I decided it was time. I felt him stiffen up. I knew it was just a matter of a couple of seconds. He moaned, “Oooooohhhhh god Jessie. I’m going to cum!”
After his moaned statement, his marvelous piece of meat contracted inside of my mouth. It was only a matter of a second or two. Then it relaxed and contracted again. A spurt of his nice salty load shot to the back of my mouth. Then another contraction, and another, and another, each one shooting a healthy amount of semen right into my willing mouth
“Damn Jessie! I have never had my cock sucked so well, or had such a powerful orgasm overtake me from any other girl.”
I smiled as a little bit of his massive load of cum dripped out of the right side of my mouth. I quickly took my finger and swept it back into my mouth. With that, I swallowed his entire load.
I went back home only to see Tracy, Brooke, and Suzy all lying naked in bed. The smell of sex was undeniably strong in the room. I kissed Tracy on the forehead and started to walk out. She stirred and woke up just before I left the room.
“Jessie? “
“Yes, hun?”
“You realize that I am not the only one that got pregnant that first night, don’t you?”
“No. I thought you were the only one.”
“No hun. All three of us are pregnant. And we will all be one big happy family together.”
I stood there looking at all three of those beautiful women in stunned silence.
Sorry for the delay since my last chapter. You may want to go back to my profile and re-read one or more chapters of my Jessie's Fantasy story.
Hope you enjoy this latest installment! Hugs
Tracy said, “Oh my god hun, you were amazing with these studs! I can’t believe that you actually let all of your friends fuck you and cum inside you!”
Fear and a slight moment of panic came across me. I wanted to run away and never see or confront my friends again. I was certain I would get the crap beaten out of me as a couple of my friends tended toward homophobia, and the sheer act of fooling them wouldn’t likely sit well with them.
Brian turned toward me in disbelief. “No way!!! There is no way that you are our friend Jesse. He doesn’t have a hot body like you do.”
“Or a sexy ass like you do!” piped in Scott.
I glanced at all of my friends and bowed my head down. I was about ready to cry. I slowly placed my hand on the back side of my head and unfastened two clips that held my wig to my natural hair, and pulled my wig off. Next, I removed my dress and turned to face them. My poor deflated boy clit was noticeable for all to see.
As I lowered my face again, I replied to them. “Yes. This is me, Jesse.”
Mark came up to me. I cowered a little as I was certain he was going to be the one that would kick my ass. He placed his hand on my cheek and lifted my face so our eyes would meet. I didn’t see any anger on his face. All I saw was one of bewilderment and confusion. After many seconds of him staring deep into my eyes and pure silence, he spoke.
“Jessie, you are one of the hottest, most sensual creatures I have ever been with. I would never in a million years guessed that you were my male friend Jesse.”
With that, he proceeded to kiss me. I was in complete shock of this turn of events. We kissed for what seemed like many minutes, and I noticed my tension and fear melted away.
Tracy pushed Mark aside and stated to him, “Don’t get too attached to Jessie. She is mine.”
What followed was several hours of my friends and I talking about the events that had unfolded over the last couple of days. There was question after question about what I felt, did I like it, who was the best, would I have sex like this again? So many questions came my way. It was all very respectful and they were treating me like a lady.
It was odd, as I was a total slut for them. But two things were certain. First, not a single one of my friends suspected at the time that I was following up on my payment. Second, I knew our friendships would never be the same, but at least I knew that they would still be friends of mine. After all of the questions and conversation, there was still the elephant in the room that no one dared to ask. Did I like it enough to continue to be Jessie and give up my life as a male? As Tracy and I were getting up to leave, Ross asked one final question.
“Jessie, what will happen after tonight? Are you going to be our male friend Jesse, or is he gone forever?”
I replied, “I’m really not sure right now.”
On the drive home with Tracy, I was a mix of emotions and conflict. We talked the entire time in the car about my future and what my plans were going to be. Let’s just say that I kept going back and forth as there were aspects of my male self that I enjoyed, and there were female aspects I enjoyed. I told Tracy, I needed to do some soul searching before I conclude what my future would look like.
Throughout the week, I continued to wear cute panties under my work clothes as male underwear, for some reason, didn’t appeal to me in the least. I really never thought of it at the time, but my mind was truly made up. That weekend, Tracy dressed me up in sexy lingerie and we made love for hours on end. It was a weekend where neither of us wanted to get out of bed. We just enjoyed exploring each other and learning how to please each other the most. I have to say that our love making was very soft, and we took our time. It was some of the most erotic and most satisfying sex that we had since we became a couple.
As the next couple of weeks went on, I started enjoying my feminine side, which meant that I always wore panties to work, and removed all traces of my male self once I got home. My phone would ring, yet I wouldn’t answer it seeing it was one of my friends. Tracy and I were still intimate with each other, but I noticed that something seemed off with her, especially when we started making love in the morning. When I brought it up to Tracy, she changed the subject.
“Hun, I know you are ignoring your friends. They really don’t deserve that. Please go out with them this weekend.”
“I don’t know,” I replied.
I started getting emotional. It was odd, but the last week I felt very emotional for some reason. This wasn’t like me in the least.
“Please call them up and talk to them.” She repeated.
I called up Brian and talked to him. After the conversation, I turned to Tracy and told her I was going to go out with my friends tonight.
Tracy smiled and said, “Oh good! I am so glad you decided to go with your friends. I’ll make sure I dig up some of your casual clothes to wear.”
I turned to her and stated, “That won’t be necessary. I would like to wear something sexy.”
Tracy looked at me and smiled.
Work seemed to drag by. I just couldn’t wait until 4PM when I would head home and get ready for a night out with my friends. When it was finally time to leave, I called up Tracy and let her know I was heading home.
After a fairly decent commute, I got home and opened the door. “Hunny! I’m home!”
Unlike every night that I came home, Tracy didn’t answer. I yelled it again, and still no answer. I walked into the kitchen and saw Tracy with her two friends Suzy and Brooke sitting around the kitchen table.
“Hi, Hun! So sorry. I didn’t hear you come in.”
“That’s OK hun. Hi, Suzy and Brooke! What’s the occasion?” I asked.
Tracy opened the conversation “Do you remember our first night together?”
“Of course I do. It was the day I approached you with my quandary. Why?”
Brooke added, “and what happened between you and Tracy?”
“Well, I remember that we had some amazing sex in the bathtub. I met you and Suzy, and... ”
Suzy interrupted, “No need to explain the entire night. So you had sex with Tracy.”
“Yes, it was amazing, and that’s when I proclaimed I loved her,” I replied.
With a big smile on her face, she said, “Hunny? I’m pregnant!”
A look of shock came across my face. Pregnant? Did the love of my life say pregnant? I certainly must be hearing things.
I finally stated the words, “Pregnant? Really? We are going to be parents?”
Tracy gave me a big kiss and said, “No.”
A look of confusion came across my face.
Tracy stated, “Not just you and I.”
I was so confused by what Tracy was saying. I started crying with joy as I hugged Tracy and started proclaiming “I’m going to be a mom!”
Tracy interrupted my happy thoughts with, “Did you hear what I said?”
“Yes, hun! We are going to be parents!”
“Yes, but it isn’t just you and I. We all are going to be parents.”
“I know! This is the best day of my life! You and I are going to have a baby together! This calls for a celebration!” I replied.
Suzy and Brooke just laughed and told Tracy, “Jessie doesn’t get it, does she?”
Tracy shrugged her shoulders, “No, she really doesn’t get it.”
I was so excited that couldn’t get my make-up on so I asked for Tracy and her friends to help me.
“I can’t wait to meet my friends and tell them the great news! I’m going to have a baby!”
Tracy, Brooke, and Suzy tried to get me to listen to their words, but I was on cloud nine. That only meant that I couldn’t comprehend what was really stated. After they helped get me ready, I kissed each of them goodbye and went to Brian’s house.
Mark and Ross were already at Brian’s house when I arrived. When Brian opened the door, his jaw just about dropped.
“Oh my god Jessie! You look so hot!”
Ross followed it up with a cat call whistle.
“Thanks, guys. You’ll never guess what I just found out! Tracy and I are expecting a baby!”
“What?” Ross questioned.
“Holy shit! Congratulations! Let’s go celebrate!” Mark shouted.
We went out to our usual hang out, only this time I was able to do so as my feminine self. We enjoyed the conversation and got a lot of laughs at the men that were hitting on me. I was feeling no pain from the celebration. This was a dangerous position for me as my inhibitions were weakening, and I was starting to flirt back to the men hitting on me.
Brian stated to me, “Jessie, we should get going and finish celebrating at my place.”
I whined, “But... But.. I like the attention I am getting.”
“You can get the same attention at a later time with Tracy,” Ross interjected.
We piled into Brian’s car and started to head back to his place. While in the back seat with Ross, I was getting frisky and started playing with his crotch. At first, Ross was pushing my hand away and stating he wanted to have fun with a real woman. It hurt my feelings to the point I was crying. I don’t understand what has been going on with my emotions lately, but damn they are so not the normal male Jesse emotions.
Ross wrapped his arms around me to comfort me, and said, “I didn’t mean to hurt you.”
When we got to Brian’s house, I was feeling happier, but also more horny. I made up my mind I was going to get into one of their pants tonight.
After many hours of conversation and my expressing my delight that I was going to be a mom for the umpteenth time, Ross and Mark left. As the fire was dying in the fireplace, I got a sudden chill so I snuggled in close to Brian. He wrapped his arms around me in an assuring way, but also bringing me closer to him. I smiled in content as he started rubbing my ass. I slowly moved my hand down to his crotch until I reached his zipper. With one slow and steady motion, I had opened the fly of his pants and reached in for my prize.
Brian looked at me and asked, “Are you sure Tracy is OK with this?”
I nodded and then moved my mouth over the tip of his nice hard shaft. Brian ever so slightly tensed up, but then relaxed as the warmth of my mouth surrounded his cock. “Mmmmm, Jessie. Where in the world did you learn to suck a cock? There is no way that you haven’t done it prior to losing your bet. You’re way too good at this.”
I paused and looked up at his eyes, “I never had another man inside of me prior to losing the bet.”
Brian couldn’t believe it. He let me continue sucking on his cock. No more words were said that night. It was just me making love to his nice hard shaft. I had put him on edge many times in order to build up his climax. After an hour of sucking him off, I decided it was time. I felt him stiffen up. I knew it was just a matter of a couple of seconds. He moaned, “Oooooohhhhh god Jessie. I’m going to cum!”
After his moaned statement, his marvelous piece of meat contracted inside of my mouth. It was only a matter of a second or two. Then it relaxed and contracted again. A spurt of his nice salty load shot to the back of my mouth. Then another contraction, and another, and another, each one shooting a healthy amount of semen right into my willing mouth
“Damn Jessie! I have never had my cock sucked so well, or had such a powerful orgasm overtake me from any other girl.”
I smiled as a little bit of his massive load of cum dripped out of the right side of my mouth. I quickly took my finger and swept it back into my mouth. With that, I swallowed his entire load.
I went back home only to see Tracy, Brooke, and Suzy all lying naked in bed. The smell of sex was undeniably strong in the room. I kissed Tracy on the forehead and started to walk out. She stirred and woke up just before I left the room.
“Jessie? “
“Yes, hun?”
“You realize that I am not the only one that got pregnant that first night, don’t you?”
“No. I thought you were the only one.”
“No hun. All three of us are pregnant. And we will all be one big happy family together.”
I stood there looking at all three of those beautiful women in stunned silence.
Sorry for the delay since my last chapter. You may want to go back to my profile and re-read one or more chapters of my Jessie's Fantasy story.
Hope you enjoy this latest installment! Hugs
Uma
- 08.11.2020
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- Category:
- Crossdressing
